Sodium Cyanide → HCID 18768971, compound

Participants

Reaction Steps

1-(Benzyl-methyl-amino)-4-phenyl-butan-2-one (2.4 g, 9.0 mmol, 1.0 equiv) was mixed in 36 mL of 2.0 M NH3 in MeOH. To the solution was added NaCN (0.484 g, 9.9 mmol, 1.1 equiv) and NH4Cl (0.528 g, 9.9 mmol, 1.1 equiv). The resulting mixture was refluxed for 2 h at which time an addition 15 mL of 2.0 M NH3 in MeOH was added and the mixture was refluxed another 4 h. Though TLC (5% MeOH in CH2Cl2) still showed the presence of the ketone, the reaction was cooled and filtered. The filtrate was concentrated and the crude product was purified by flash chromatography on SiO2 using 60% hexanes in CH2Cl2 then 1.5% MeOH to 3% MeOH was added. The desired product was isolated pure (0.561 g, 21%) as a yellow oil that crystallized upon standing at −20° C.; MS, m/z 294=M+1.

Provenance & Evidence