Water → HCID 18477102, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.), stirred mixture of n-butyllithium in hexane (1.6 M, 34.7 cm3) and diethyl ether (25 cm3) was added 4-bromobenzotrifluoride (7.8 g). After a further 15 min, 2-(N-benzylmethylamino)methyl-3,4-dihydro-2H-naphthalen-1-one hydrochloride (prepared using methods described in Process 1) was added portion-wise. The reaction mixture was then stirred for 1 h before being allowed to warm to room temperature and then water (50 cm3) was added. The organic layer was separated and washed with water (50 cm3). It was then extracted with hydrochloric acid (2 M, 50 cm3) and the acidic aqueous portion was basified with solid sodium carbonate and extracted with dichloromethane (100 cm3). The combined organic extracts were dried (Na2SO4) and the solvent was removed under reduced pressure to afford the title compound as a colourless oil.

Provenance & Evidence