Methylamine → HCID 12951846, compound

Participants

Reaction Steps

A mixture of 3-(4-chlorophenyl)-3-hydroxy-N-methylpropylamine (prepared by borane-THF reduction of β-p-dichloropropiophenone followed by reaction of the resulting chloro-alcohol with methylamine in ethanol) (10 g, 50 mmM), 2,2,6,6-tetramethylpiperidine (8.4 ml, 50 mM), o-fluorobenzyl chloride (7.25 g, 50 mM) and acetonitrile (100 ml) was stirred for 24 hours at ambient temperature. The mixture was filtered, the filtrate evaporated and the residue partitioned between 2 N hydrochloric acid and ether. The aqueous layer was basified and extracted with dichloromethane. The organic phase was dried, evaporated and the residue recrystallised from 60°-80° petrol to give the title compound (8.8 g) m.p. 52°-4° C. Found: C, 66.0; H, 6.2; N, 4.4%; C17H19ClFNO requires: C, 66.3; H, 6.2; N, 4.6%.

Provenance & Evidence