4-Fluorobenzonitrile → HCID 12875685, compound

Participants

Reaction Steps

A mixture of N,N-dimethyl-3-hydroxy-3-phenylpropylamine (3.58 g, 20 mM), 50% sodium hydride dispersion (1 g) and DMSO (50 ml) was heated at 80° until homogenous, cooled to ambient temperature and treated dropwise with a solution of 4-fluorobenzonitrile (2.42 g, 20 mM) in DMSO with cooling (exothermic). After 1 h the reaction mixture was poured on to water (200 ml) and extracted with ether (2×200 ml). The ether extract was extracted with 1 N hydrochloric acid (2×50 ml), the acid extract basified and then extracted with ether (2×200 ml). The ether was dried and the solvents removed under reduced pressure to give an oil which was dissolved in ethyl acetate and treated with an excess of a solution of oxalic acid dihydrate in ethyl acetate. Removal of the resultant precipitate by filtration followed by recrystallisation from ethyl acetate gave the title compound (4.8 g) as the oxalate quarter hydrate m.p. 80° (decomp). Found: C, 64.1; H, 6.05; N, 7.7% C18H20N2O.C2H2O4 requires: C, 64.1; H, 6.1; N 7.5%.

Provenance & Evidence