NaBH(OAC)3 Reductive Amination

[fanofshulgin]

I was talking to a gentleman onboard a spaceship last night, and he happened to mention that he took 1mmol of a fragrant  ketone (i am personally guessing camphor ) in DCE (10ml) to which was added NaBH(OAC)3 (2mmol) and a low molecular weight amine HCl salt (1.5mmol).  This was stirred, and Et3N (2mmol) was added.  TLC after 24 hours showed the presence of starting material apparently.....so my travelling companion then seemingly added another 1 eq of Et3N.  After another 24 hours he said everything had gone to completion. Did he mean his marriage plans ? Travelling ? Lifes ambitions? I dont know, but he was a very happy sort of character.  He confused me when he said that a simple acid/base extraction followed by a cowboy distillation affored very pure product, which crystallised wonderfully from IPA/Et2O.

He was a very strange man...he stopped talking and i was a little bored - luckily the inflight movie was excellent!

PS - in his sleep, he was blabbering about how "it only went to 65% in DCM" and that "DCE was the key"...wasnt he a strange one!

[Vitus_Verdegast]

Did the man also mention his final yield using DCE ?

[yellium]

then seemingly added another 1 eq of Et3N. [...] He confused me when he said that a simple acid/base extraction followed by a cowboy distillation affored very pure product, which crystallised wonderfully from IPA/Et2O.

You sure your product isn't Et3N.HCl?

[fanofshulgin]

......
With DCE, the reaction was quantitative (small loss from distallation only)

sorry, crystallised from IPA/conc HCl added Et2O until lasting turbidity ala shulgin.

[fanofshulgin]

Of course, what he didnt mention at the time was that he removed all volatiles under vaccum at 80C, which removed all Et3N.  Analysis of final product confirmed this.