The Hive => Newbee Forum => Topic started by: Lestat on June 19, 2004, 06:57:00 PM
Title: Homebrew pyridine to piperidine?
Post by: Lestat on June 19, 2004, 06:57:00 PM
Has anybee had an idea like this? Reducing an alkyl nitrite to the nitrate and heating the product with phosphorus pentoxide to make pyridine, then usind the action of nascent hydrogen to form piperidine?
I can't see any reason why this wouldnt work, and the nitrites are freely available as "poppers" this seems to me to be an intersting and possible novel procedure for producing piperidine. Any comments or ideas on this bees? ;D
Title: Reduce to what?
Post by: Nicodem on June 20, 2004, 01:25:00 AM
Could you at least explain what are you talking about? Claims like "reducing an alkyl nitrite to the nitrate" are complete nonsense. If you reduce something its oxidation state goes down not up. Besides what do amylnitrite or butylnitrite, the so called poppers have to do with piperidine or pyridine?
Title: I apologise...
Post by: Lestat on June 20, 2004, 10:34:00 AM
I must apologise, that was not the most coherent thing I have ever written if you understand, but I was referring to treating the alkyl nitrite with phosphorus pentoxide, to produce pyridine, then bubbling nascent hydrogen through the pyridine to make piperidine. I was thinking the poppers would just be a convenient source of the nitrite to start with ;D
Title: Do you have any reference for the reaction of...
Post by: psyloxy on June 20, 2004, 05:31:00 PM
Do you have any reference for the reaction of alkyl nitrites with phosphorous pentoxide ?
Sounds interesting but unlikely.
--psyloxy--
Title: One reference comin' right up
Post by: Lestat on June 20, 2004, 05:35:00 PM
Found it while I was bored, just dicided to look up a random chemical, and chose pyridine ;D
Title: Ann., 1868, Sup p1. 6, p.
Post by: psyloxy on June 20, 2004, 07:59:00 PM
Ann., 1868, Sup p1. 6, p. 329 says to use iso-amylnitrate. Would require you to to find a specific brand of 'poppers' that consists only of iso-amylnitrite. I'm not into poppers so I don't know exactly, but I thought amylnitrite (which is not even the iso that you want) was taken off the shelves.
You cannot just take any alkyl-nitrate. --psyloxy--
Title: Yes I know that isoamylnitrate isn'y used as...
Post by: Lestat on June 20, 2004, 08:04:00 PM
Yes I know that isoamylnitrate isn'y used as 'poppers' The reference to poppers was that, at least here in the UK, isobutyl nitrITE is used for that very purpose, all I meant was that can't the isobutyl analogue be used in the same reaction? or will the lower alcohols not give the desired results?
Title: nope
Post by: psyloxy on June 20, 2004, 08:09:00 PM
No. Different starting material, different product, or no reaction at all.
--psyloxy--
Title: (Iso)amyl alcohol shouldn't be impossible to...
Post by: Lestat on June 20, 2004, 08:28:00 PM
(Iso)amyl alcohol shouldn't be impossible to obtain, and I doubt any alcohol other than pinacolyl is watched or restricted, maybe this is a possible route for more well equipped bees to think about.
Title: Nitrate =/= nitrite
Post by: Nicodem on June 21, 2004, 12:15:00 AM
It says: "by heating isoamyl nitrate with phosphorus pentoxide (E. T. Chapman and M. H. Smith, Ann., 1868, Sup p1. 6, p. 329)". Nitrate is not the same as nitrite. You can't get any nitrate from any poppers. Nitrates are esters of nitric (V) acid while nitrites are esters of nitric (III) acid. Amyl nitrate is n-pentyl nitrate [ CH3-(CH2)4-O-NO2 ] while isoamyl nitrate is isopentyl nitrate [ (CH3)2CH-(CH2)2-O-NO2 ]. The problem is that both amyl and isoamyl are used completely wrong so often isoamyl is the same as amyl and amyl the same as isoamyl (trivial names sucks). Just the thought that somebee wants to waste something so useful as P2O5 just to produce pyridine breaks my heart. ::)
Edit: I have checked and both, amyl and isoamyl, are supposed to bee trivial names for isopentyl. But n-pentyl is also called n-amyl in some cases.
Title: As you can tell...
Post by: Lestat on June 21, 2004, 08:48:00 AM
As you can tell, I'm only a newbee :( , but I'm a fast learner, I guess I just made a bad on this one.
Title: glutaraldehyde + hydroxlyamine = pyridine + 3 h2o
Post by: xxxxx on June 21, 2004, 08:58:00 AM
i read in an encyclopedia that 1,5 dicarbonyl compounds when reacted with hydroxylamine produce pyridines plus three moles of water. you could get small amounts (30 grams per kilo) of piperidine by extracting its amide from black pepper with ethanol.