Aluminium lithium hydride → N-({2-chloro-5-[3-(methyloxy)propyl]phenyl}methyl)cyclopropanamine

Participants

Reaction Steps

LiAlH4 (5.70 g, 151 mmol) was added in portions to a sol. of 2-chloro-N-cyclopropyl-5-(3-methoxy-propyl)-benzamide (10 g, 37.7 mmol) in THF (230 mL) at 0° C. The ice bath was removed, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt, and was cooled to 0° C. Water (7.5 mL), aq. 15% NaOH (17 mL), and water (5.7 mL) were carefully added. The mixture was filtered, and the precipitate was washed with EtOAc. The filtrate was evaporated under reduced pressure. The residue was diluted with EtOAc, and the resulting mixture was washed with water, and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:4→1:3→1:2) yielded the title compound (5.60 g, 59%). LC-MS: tR=0.86 min; ES+: 254.19.

Provenance & Evidence