Hydrochloric Acid → HCID 18663626, compound

Participants

Reaction Steps

At 50° C. a solution of 0.5 ml (1.74 mmol) of 10-bromomethyl-dibenz[b,F]oxepine is squirted into a solution of 0.3 ml (4 mmol) of allylamine in 0.9 ml of anhydrous methanol and the mixture is stirred for 30 minutes. Tert-butyl methyl ether and ethyl acetate are added and the mixture is extracted 3× with 20 ml of 1N hydrochloric acid each time, the combined aqueous phases are rendered basic with potassium hydroxide pellets and extracted 2× with ethyl acetate, and the organic phases are dried over sodium sulfate and concentrated. 0.35 ml (0.7 mmol) of 2N ethereal hydrochloric acid is added to the crude amine (180 mg) in 2 ml of diethyl ether, and the precipitated white hydrochloride is washed with diethyl ether and dried under a high vacuum at 40° C. 200 mg (667 μmol)=39% of the title compound alias 10-allylaminomethyl-dibenz[b,f]oxepine are obtained in the form of white crystals; melting point: 148°-158° C.; 1H-NMr (CD3OD, 200 MHz). 3.74 (d, 2H); 4.35 (d, 2H), 5.55 (m, 2H); 5.95 (m, 1H); 7.20-7.58 (m, 9H); MS: 263 (M+, free base), 222, 208, 181, 165, 152.

Provenance & Evidence