4-Methoxybenzylamine → HCID 69181089, compound

Participants

Reaction Steps

To a solution of 4-methoxybenzylamine (5.6 g, 41.2 mmol) in methanol (100 mL) was added methyl 3-formylbenzoate (5.2 g, 31.7 mmol) at ambient temperature. The solution was stirred for 30 minutes and sodium cyanoborohydride (3.0 g) was added. The mixture was stirred at ambient temperature overnight and concentrated to about 20 mL. Water (100 mL) was added and the mixture acidified with 2N hydrochloric acid to a pH of 3. The mixture was partitioned between ethyl acetate and brine and the organic phase separated and concentrated. The residue was purified by flash chromatography on silica gel using 10% methanol in ethyl acetate to give 6.0 g (67%) of the title compound. MS (DCI): m/z 286 (M+H)+.

Provenance & Evidence