Hydrochloric Acid → HCID 16228062, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, add borane-dimethyl sulfide complex (8.7 mL, 17.4 mmol, 2M solution in THF) to a solution of 4-[(N-methyl-iso-propylamino)-methyl]-benzonitrile (660 mg, 3.51 mmol) in THF (20 mL) at room temperature then heat to reflux for 30 min. Cool the mixture in an ice-bath and carefully add methanol (10 mL). Warm the mixture to room temperature and add concentrated HCl (10 mL). Stir the mixture for 12 h, and concentrate in vacuo. Purify by chromatography on silica gel (25 g) eluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound (550 mg, 82%). MS (ES+) m/z: 193 (M+H)+.

Provenance & Evidence