N-Ethylhydroxylamine hydrochloride → 2-(6,11-dihydrodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine

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Reaction Steps

2-(6,11-Dihydrodibenz[b,e]oxepin-2-yl)ethanol methanesulfonate (13.5 g) was taken up in 20 ml of absolute ethanol and added to a solution containing ethyl hydroxylamine hydrochloride (11.03 g) and potassium t-butoxide (12.7 g) in 600 ml of absolute ethanol. The mixture was stirred at reflux under a nitrogen blanket for 18 hours then evaporated. The residue was taken up in chloroform and washed with brine, dried, and evaporated. Purification of the residual oil (HPLC, 9:1 DCM-methanol) gave an oil which crystallized from ether-hexane. Recrystallization from ether-cyclohexene gave 1.7 g of 2-(6,11-dihydrodibenz[b,e]oxepin-2-yl)-N-ethyl-N-hydroxyethylamine, as crystals, m.p. 102°-103° C., with softening at 88°0 C.

Provenance & Evidence