Dichloromethane → HCID 18663592, compound

Participants

Reaction Steps

A mixture of 1.1 g (3.044 mmol) of N-(dibenz[b,f]oxepin-10-ylmethyl-prop-2-ynyl-carbamic acid tert-butyl ester and 1.45 ml of methanesulfonic acid in 1 ml of dioxane and 9 ml of dichloromethane is stirred for 1 hour at room temperature, 2N sodium hydroxide solution is added and the mixture is extracted 2× with dichloromethane. The organic phase is concentrated using a rotary evaporator, taken up in ethyl acetate and extracted 3× with 1N hydrochloric acid, and the aqueous phase is rendered basic with potassium hydroxide pellets, extracted 3× with dichloromethane, dried over sodium sulfate and concentrated. The crude light-brown oil is dissolved in 2N ethereal hydrochloric acid and concentrated. The crude hydrochloride (beige crystals) is recrystallised from ethyl acetate/methanol. 386 mg (1.30 mmol)=42% of N-(dibenz[b,f]oxepin-10-ylmethyl)-N-prop-2-ynylamine hydrochloride alias 10-propargylaminomethyldibenz[b,f]oxepine hydrochloride are obtained in the form of white crystals; melting point: 181°-183° C.; MS: 261 (M+, free base), 222,181, 165, 152.

Provenance & Evidence