[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrile → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of [4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-acetonitrile (preparation 104), (1 g, 4.1 mmol) and Raney® nickel (100 mg) in 2M methanolic ammonia (35 mL) was stirred under 60 psi of hydrogen gas at 50° C. for 6 hours. Tlc analysis showed that not all of the starting material had been consumed and so further Raney® nickel (200 mg) was added to the reaction mixture and heating continued for 5 hours. Tlc analysis again showed that starting material was still present and so additional Raney® nickel (200 mg) was added and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was then filtered through Arbocel® and was concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography using a 4 g RediSep® silica cartridge, eluting with dichloromethane:methanol:0.88 ammonia, 85:15:1.5 to 80:20:2, to afford the title compound in 16% yield, 160 mg.

Provenance & Evidence