Methanol → N2-Acetyl-L-glutamine

Participants

Reaction Steps

A stirred solution of 122 g (0.495 mol) of racemic 1-(2-piperidino-phenyl)-3-methyl-1-butylamine in 1000 ml of acetone is mixed with 93.7 g (0.495 mol) of N-acetyl-L-glutaminic acid. The mixture is refluxed over a vapour bath and methanol is added in batches (a total of about 80 ml) until a clear solution is obtained. After this has been left to cool and stand overnight at ambient temperature, the crystals obtained are removed by suction filtering, washed twice with 200 ml of cold acetone at -15° C. and then dried. The product obtained [98.9 g; melting point: 163-166° C.; [α]D20 =+0.286° (c=1 in methanol)] is recrystallised from 1000 ml of acetone with the addition of 200 ml of methanol, thereby obtaining the (S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine as the addition salt of N-acetyl-L-glutaminic acid.

Provenance & Evidence