For your consideration, revised in BOLD
Hope this helps. Report back with results!
1. To a 2-neck 2000 mL RB flask set in an ice bath and containing a stirbar is added 45.5g of methylamine hydrochloride which is then carefully dissolved in the minimum amount of water needed. Stirring is begun, and the amount of water used is recorded.
2. Add an amount of dry toluene that is 10X the volume of water just used in the above step.
3. Slowly add 27g of NaOH using a powder funnel. (1 mol eq compared to the methylamine.hcl used)
4. Then add additional NaOH in the amount of 8g for every milliliter of water used in Step 1. So for example if it took 50mL water to dissolve the methylamine, 400g dry NaOH would be added.
5. Then add 27g more NaOH to account for the water formed by the reaction between OH(-) and MeNH3(+) (1 mol eq compared to methylamine.hcl used)
6. Unclamp the reaction flask, remove the stirbar, stopper the necks, and swirl/shake the contents well to mix thoroughly. Immediately check for and release any pressure buildups. Replace flask in the ice bath, clamp it again, and allow all solids to settle. This must be done several times over the course of 30 minutes.
7. After the mix has settled, unclamp the flask and decant the (upper) toluene phase into a separatory funnel, taking care not to let any of the lower aqueous phase contaminate it. If you're like me you will fastidiously finalize the separation using the separatory funnel, avoiding all traces of the aqueous phase with extreme prejudice (this kind of hypervigilant separation is a personal quirk of mine; others may want to simply decant once and/or pour through a fluted filter). Cover or cap the vessel used to temporarily hold the toluene/amine phase to protect it from atmospheric moisture. Pour the aqueous phase into a beaker and set aside, out of the way.
8. Clean out and dry !!!! the original reaction flask, place the stirbar back into it, and return the toluene/amine phase to it.
9. Then add 500 ml dry MeOH and 100g ketone, and return it to the ice bath. Reclamp the flask, affix the thermometer, stopper the other neck, and begin medium stirring. Stir for 30 minutes. at least
10. After 30 minutes, increase the stirring speed so that it's quite vigorous and add, via a number of small portions, 10.4g NaBH4 (or up to [?]g depending on the freshness/staleness of the NaBH4 this is up to you, cant tell you how degraded your borohydride is ). Some frothing will be visible upon the additions (between additions, loosely restopper the neck H2 production does occur due to decomposition of the borohydride without reduction, this HAS to be vented or will shatter your glass!)
NOTE: Judge the amount of the portions and the time between additions by monitoring the temperature. Add the borohydride at a rate which is slow enough to keep the temperature below 10°C. So start by adding say 0.5g once and then watching the temperature. It will rise on addition of the borohydride and will drop back when most of it has reacted or has gone into solution. Adjust the amounts until the sweet spot is found---the rate at which the temperature stays low, but doesn't take all day to add the borohydride. the first few additions may not generate so much heat, but heat is stored in the liquid phase (heat exchange rates and all that, to the physics inclined) and will build up upon subsequent additions, so dont let it fool you.
Whatever color had formed in the imine formation step gradually disappears during the NaBH4 additions to give a white/yellow opaque mixture. Very good stirring continues to be needed here. If you have an overhead stirrer, this is a must for good yields in the larger batches. Otherwise (smaller to medium scale), increase stirring as much as is possible without stirbar instability.
11. After the addition of the NaBH4 is complete, allow the mix to stir rapidly for two hours at room temperature.
12. When the reaction mixture has been stirred for the two hours, an addition funnel is filled with [?] (*see note at end) mL of ~50% W/V acetic acid and attached to the flask. The residual borohydride is then destroyed by cautious dropwise addition of the acid until the gas evolution stops and pH 3 is reached (in other words, when gas evolution begins to visibly diminish, start testing pH). This is done with fume hood and mask, or outdoors with a breeze, as the gases evolved are highly toxic diborane and highly flammable H2. ive never worn a mask when doing this, but i do carry all my reactions in the hood. besides, diborane isnt all that bad. H2 is bad though, since it ignites super easily
NOTE: When quenching with the acid, a type of goo (borax or something similar) forms which gradually goes mostly back into solution. With larger batches an overhead stirrer is an absolute must, since this goo can be hard on magnetic stirrers.
13. A distillation apparatus is set up, and the alcohol is then removed by vacuum distillation. When the alcohol has finished coming over, the heat to the setup is turned off and the setup allowed to cool to room temperature. When cooled, the vacuum to the glass is released and the setup is dismantled. I use a rotary evaporator. if you dont own one yet, get one. they can be had on ebay. do not distill the toluene away.
14. The remaining aqueous/toluene solution is transferred to a separatory funnel, then extracted once with 50 mL DCM to recover any unreacted ketone. The DCM/ketone is appropriately labeled and set aside for future recovery. never tried this trick, dont know how it will work with the toluene that is also left... anyway DCM is known to cause emulsions for newbies, so advocating its use in a writeup is wrong. a better bet would be to use additional toluene in dcm's stead
15. The aqueous solution is then taken to pH 12 to 13 with 25% NaOH and extracted twice with 50 mL toluene and then once with 75 mL toluene. i would do either 4x50-100ml or the like. the smaller the volume the cleaner is the extraction, and the more times you extract, the more product you get
16. The toluene extractions are combined and then washed twice with a small portion of distilled water to remove trace NaOH. and then once with brine (this raises the ionic strength of the water, giving better final separation of the water
17. The toluene/product is then dried with MgSO4 (MgSO4 is slightly acidic. Other drying agents such as Calcium Sulfate, Na Sulfate and the likes are adequate as well. few hours are required for "thorough" drying, however if youve used toluene and choose to distill you oil, during the evaporation of toluene you will dry it as well due to the toluene/water azeotrope filtered, and gassed with dry HCl to form the crude salt (or optionally, salted by one's technique of choice).
I never gas. i always rotovap the solvent away, then distill the oil, dissolve in a dry solvent of choice, and add dry acid of choice to make the salt. Alternatively, I add concentrated hcl to a methanol solution of the oil, then rotovap all the methanol away and spread the aq./solid salt in a shallow pan to fully evaporate.
18. The crude salt is collected by filtration, dried of residual toluene, weighed, and then recrystallized with isopropyl and acetone (or by one's preferred solvent pair or method). Ive found water to be a very good recrystallization solvent. also ipa/hexanes works well for me.
19. Have a cold beer and a fat joint. You've earned it.
Acetic Acid Note : a safe amount would be 1mol eq. with respect to the borohydride added, so at least 17-18g (predilution) of glacial acetic acid as a ball park measure. Depending on the amount of goo you get (amount of borohydride, purity of borohydride) you might need alot more or alot less.
Hope this helps. Report back with results!

