Sodium Hydroxide → N-(4-chloro-3-cyclopropylaminomethylbenzyl)propionamide

Participants

Reaction Steps

Cyclopropylamine (1.28 mL, 18.2 mmol) was added to a sol. of N-(4-chloro-3-formyl-benzyl)-propionamide (2.74 g, 12.1 mmol) in MeOH (42 mL). The mixture was stirred overnight, and NaBH4 (918 mg, 24.3 mmol) was added in portions. The mixture was stirred for 4 h, and aq. 1M NaOH (70 mL) was added. The solvents were partially removed under reduced pressure, and the aq. residue was extracted with EtOAc (2×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC(CH2Cl2→MeOH/CH2Cl2 1:9) yielded the title compound (2.62 g, 81%). LC-MS: tR=0.58 min; ES+: 267.38.

Provenance & Evidence