Hydroxyamine hydrochloride → 1-benzyl-4-chloro-5-hydroxyiminomethyl-2,3,6,7-tetrahydro-1H-azepine

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Reaction Steps

A solution of 5-chloro-1-(phenylmethyl)-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde (may be prepared as described in Description 3) (11.6 g, 46.5 mmol) in ethanol (100 ml) was stirred with hydroxylamine hydrochloride (3.23 g, 46.5 mmol) at room temperature for 72 hours. The ethanol was removed by evaporation and the residue partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The ethyl acetate was washed with water & brine, then dried and evaporated to afford the title compound (D4); MS (ES+) m/e 265 & 267 [M+H]+.

Provenance & Evidence