Benzylamine → HCID 22033754, compound

Participants

Reaction Steps

Benzylamine (107 mg, 1.0 mmol) was suspended in a mixture of ethanol (0.5 ml) and water (1.5 ml). To the resulting suspension were successively added potassium cyanide (65 mg, 1.0 mmol) and sodium bisulfite (104 mg, 1.0 mmol) under ice cooling and stirring. An ethanol (1.5 ml) solution of 1,1-cyclopropane dicarboaldehyde (98 mg, 1.0 mmol) was added dropwise and the mixture was stirred at the same temperature for 2 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over sodium sulfate, filtered, and then evaporated under reduced pressure. The oily residue thus obtained was subjected to chromatography on a silica gel column (silica gel 8.0 g; hexane:ethyl acetate=5:1), whereby the title compound (109 mg, 50.8%) was obtained as a slightly yellow oil.

Provenance & Evidence