sulfate/antihistamine removal

[jemma_jamerson]

after being away for six months swims fav pills are off the shelf here in oz.

swim found some sudo 120mg sulfate pills containing an anti hist.

swim is guessing that a simple a/b will convert the sulfate to hcl and remove the anti hist? i have since UTFE to read that apparently the anti-hist is removed by the a/b i think it was placebos post. so thats all it takes for these pills no dry acetone boil??

ideas please

[wareami]

The Orange Gaaks mate...
Not sure how prevailant they are in OZ but from AWE accounts they are hot and heavy over down under....
TCE removes antihists and Ibee seriously doubts that a simple a/b would remove them or the earlier hcl pfed formulations wouldn't have been blue after a/b extractions.
The sulfate form needs the a/b to convert it from the sulfate...but one might want to look at removing the poly's and antihists first.
Then if OIIgaak is present some japandrier might be in order.
Just a thought.

[jemma_jamerson]

not sure about the organge gakk ill have to test it to find out.

TCE is?  

i have read that an a/b removes the anti hist, abit confusing.

so swim would do a dry acetone boil to remove the anti hist?
then a/b? going on the notion that the orange gakk isnt there?

[beez_neez]

Hi mate. I know the pill's of which you speak and yes they are full of orange gakk!
Swibn has played with these suckers and initial attempts yeilded 1/3g per box but with a little practice, 1g per box is now acheived.
In breif;
1) 2x dry tone boils
2) 2x dry toluene boils
3) Add basing medium(methanol works best)
4) IMPORTANT! basify with sodium carbonate(equal to that of pill mass). Stir like crazy.
5) 3x toluene pulls.
6) boil off methanol and gas/titrate for hcl, or just evap the whole lot for f/b.
I can give you some improvements once you have mastered this.PM me then.
Just been to up your way for holiday.Fuckin hot dude!

[Master_Alchemist]

Had a crazy dream last night, went a little like this:
Found 90x60mg Suzy Hcl, 2.5mg Tripolidine(antisneeze) tabs!
1.Soaked the bastards in otc mineral turps for 10hrs.
2.Decanted turps, rinsed with AR acetone, heated/stirred PM/Tone for about 5min.
3. 5:5:5.4g, NaOH, NaCI, available Suzy in PM, mixed extensively for 2 minutes.
4. AR methanol was added in very small quantities to get a nice thin paste. After few minutes of stirring temp soared so a touch of xylene was added. 10min manual stirring total.
PM turned an attractive warm yellow colour (good sign!)
5. To PM was added Xylene and stirred for 20min.
Sediment settled & xylene was drained. Repeated 3 times.
6. Combined xylene was washed 3 times with dH20 of varying temperature, Ph was kept at 10. Below 9 and your in strife!
7. Xylene was gassed with HCl gas which crystallised nicely.
8. Crystals were filtered and rinsed in AR acetone, then dissolved in hot AR methanol & crystallised.
Repeated process 3 times for good luck!
Obtained around 4.3g Suzy Hcl from 5.4g available  
Around 80% yield, which isnt bad considerng I was told to expect 65%...In the dream of course. Well time to wake up now, I smell speed on toast, Later guys.

[wareami]

Well...if bees aren't too concerned about all the boiling, then there are a few proven methods that battle the whole lot.
I know Ibee isn't in a position to boil aromatic solvents.
All his procedures require roomtemp chems and extractions.
Geez or maybe some others can explan in better detail the process of removing OII gaak using the same methods similar to beezneez with the boiling tolly andc tone.
Somehow that always seemed a viable method for removing OII gaak but Ibee just couldn't perform the feat due to nosey neighbors.
100ml tetra
10ml JD
Mix thoroughly then give the GUPS a bath...(no more than 3 minutes)
Pour the whole mess through a single filter and then dry the filtercake....pass through a fineseive strainer.
3 times the amount of alky over gups
let set til clear then pull alky/pfed and pass through fine filtration....
Evap alky and scrape up blue xtals.
Wash the xtals with tone until all blue is gone!
There ya have it!

[jemma_jamerson]

only one problem no toluene here in this place  
can i substitute the toluene for any thing?

[callen]

Boil in turps 15-mins. Filter. Boil the solids of the filter cake in a xx-chloromethane or xx-chloroethane solvent, xx- being per-, di-, or tri-. Filter. Dissolve solids in ICE cold (after 15-min. in the freezer) alcohol (methyl, ethyl, whatever). Evap the alcohol. Nice xtal mass is the resultant product left in the dish.

[geezmeister]

Might I add, to Beez_Nees propsal, that you also wash the nonpolar solvent before gassing with a weak NaOH solution a time or two, then the water washes?

That seems to help in removing OII.

I would definitely suggest gassing for the salt form, then dissolving the pseudo HCl in MeOH, rinsing the filter with MeOH, pouring all the MeOH/pseudo solution into xylene or a 50/50 mix of xylene and naptha, heat to 105 fairly rapdily, and allow the pseudo HCl to precipitate. Filter while hot, rinse with acetone, dry, and react.

[jemma_jamerson]

callen these are sulfate so an a/b is needed

swim just got this from a fellow ozy bee

as a general extract technique for pfed SO4/antihistamine formulations, SWIC will crush em, boil in acetone for 5 mins with stirring, decant tone, let dry completely, extract twice thoroughly with water then filter.

to the water extract is added small portion of NP, and with stirring NaOH is added in small proportions. this slowly bases the extracted pfed sulfate, and it instantly dissolves in the NP. (well, toluene at least, ive heard xylene has similar properties) keep basing at a slow rate until the orange beast gets activated, basing slowly with stirring ensures that all pfed is absorbed before the orange-agent kicks in and foils your plans!

then evap toluene for FB (my favourite) or titrate it with HCl for your HCl salt

beez_kneez thank fawk for that info bro, yes it is as hot as a rattle snakes arsehole here, try training in this weather  

ill have to pm you to get a little bit clearer details mate, fuckin orange crap, you go away fopr six months and the shit hits the fan  

[SHORTY]

I decant the xylene without filtering.  If you use a visionware sauce pan instead of a beaker it works very well.  The visionware stays hot longer than a beaker does so if you take the temp to 105C and allow the pseudo to settle for no more than a minute and slowly tilt the pan, the pseudo will remain on the bottom allowing you to tilt the pan nearly 90 degrees to let the last of the xylene drip out.  Then flood with acetone and it will immediately start boiling.  Stir and decant while still hot.

[Zen]

Monograph Number:  9817
Title:  Triprolidine
CAS Registry Number:  486-12-4
CAS Name:  2-[(1E)-1-(4-Methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl]pyridine
Additional Names:[/b]  trans-2-[3-(1-pyrrolidinyl)-1-p-tolylpropenyl]pyridine;  trans-1-(2-pyridyl)-3-pyrrolidino-1-p-tolylprop-1-ene;  trans-1-(4-methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-ene
Molecular Formula:  C19H22N2
Molecular Weight:  278.39. 
Percent Composition:  C 81.97%, H 7.97%, N 10.06%
Literature References:  Histamine H1-receptor antagonist.  Prepn:  Adamson, US 2712020; US 2712023 (both 1955 to Burroughs Wellcome); Adamson et al., J. Chem. Soc. 1958, 312.  Structure-activity studies:  Ison, Casy, J. Pharm. Pharmacol. 23, 848 (1971).  Crystal and molecular structure:  James, Williams, Can. J. Chem. 52, 1880 (1974).  Pharmacokinetics and antihistaminic effects in humans:  K. J. Simons et al., J. Allergy Clin. Immunol. 77, 326 (1986).  Comprehensive description:  S. A. Benezra, C.-H. Yang, Anal. Profiles Drug Subs. 8, 509-528 (1979).
Properties:  Crystals from light petr, mp 59-61°.  uv max (ethanol):  236, 285 nm (e 15300, 6800).
Melting point:  mp 59-61°
Absorption maximum:  uv max (ethanol):  236, 285 nm (e 15300, 6800)
Absorption maximum:  uv max (ethanol):  236, 285 nm (e 15300, 6800)

Derivative Type:  Hydrochloride monohydrate
CAS Registry Number:  6138-79-0
Manufacturers' Codes:  295C51
Trademarks:  Actidil (Wellcome);  Actidilon (Wellcome);  Pro-Actidil (Wellcome);  Pro-Entra (Wellcome-Sumitomo);  Venen (Tanabe)
Molecular Formula:  C19H22N2.HCl.H2O
Molecular Weight:  332.88. 
Percent Composition:  C 68.56%, H 7.57%, N 8.42%, Cl 10.65%, O 4.81%
Properties:  Crystals from water, mp 116-118°.  uv max (ethanol):  235, 283 nm (e 15000, 7400).  Moderately sol in water, ethanol, methanol.
Melting point:  mp 116-118°
Absorption maximum:  uv max (ethanol):  235, 283 nm (e 15000, 7400)

Derivative Type:  Oxalate
Molecular Formula:  C19H22N2.C2H2O4
Molecular Weight:  368.43. 
Percent Composition:  C 68.46%, H 6.57%, N 7.60%, O 17.37%
Properties:  Crystals from methanol, dec 173-174°.  uv max (ethanol):  233, 283 nm (e 16200, 8200).
Absorption maximum:  uv max (ethanol):  233, 283 nm (e 16200, 8200)
Therap-Cat:  Antihistaminic.

[Zen]

SOLUBILITIES:
  Water: >=100 mg/mL @ 20 C (RAD)
  DMSO: >=100 mg/mL @ 20 C (RAD)
  95% Ethanol: >=100 mg/mL @ 20 C (RAD)
  Methanol: Moderately soluble
  Acetone: 10-50 mg/mL @ 20 C (RAD)
  Toluene: Not available

OTHER SOLVENTS:
  Ether: <1 mg/mL
  0.1 N HCl: 319 mg/mL
  n-Octanol: 75 mg/mL
  Chloroform: 480 mg/mL
  Propylene glycol: 237 mg/mL
  Alcohol: Soluble in 1.5 parts

[Zen]

    " Acetone Soxhlet @ 57° C. "


For the T.HCl atleast.

The T.FB could be distilled over at 61° C.

Then the Pseudo.FB around 118° C.

Unless you have vacuum.  

*****

    Reminds me of the moonies and their moonshine:

"You nevar wanna drink the stuff that comes'cross first, ya hear?".