Sodium hydride → 2-Phenyl-2,3,4,5-tetrahydro-[6H]-1,5-benzoxazocine

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Reaction Conditions

Reaction Steps

A mixture of N-(2-fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine (4.5 g, 17 mM), 50% sodium hydride dispersion (870 mg, 17 mM) and dimethylsulphoxide (200 ml) was stirred for 24 hours at 50° C. under argon. The mixture was cooled to ambient temperature, poured onto water (700 ml) and extracted with ether (3×200 ml). The combined ether layers were extracted with 1 N hydrochloric acid (3×50 ml), the acid layer basified and extracted with ether (2×200 ml). The organic phase was dried and the solvent removed under reduced pressure. Recrystallisation from cyclohexane gave the title compound (1.7 g) m.p. 73°-4° C. Found: C, 80.1; H, 7.4; N, 5.9%; C16H17NO requires: C, 80.3; H, 7.2; N, 5.9%.

Provenance & Evidence