Ammonia → HCID 9991164, compound
Reaction equation
Br[CH2:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[NH3:18]>C1(C)C=CC=CC=1>[CH:17]1[C:5]2[CH:4]=[C:3]([CH2:2][NH2:18])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=[CH:15][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.0 g (3.48 mmol) of 10-bromomethyl-dibenz[b,f]oxepine in 3 ml of toluene is added dropwise at 40° C. to 30 ml of NH3 -saturated methanol and the mixture is stirred at 35°-50° C. for 1 hour and at room temperature overnight. The solvent is partially removed, and the reaction mixture is taken up in tert-butyl methyl ether, washed with 0.1N sodium hydroxide solution and extracted with 1N hydrochloric acid. The aqueous phase is rendered basic with sodium hydroxide pellets and extracted with tert-butyl methyl ether, the organic phase is dried over sodium sulfate and the solvent is removed. 349 mg (1.56 mmol)=45% of N-(dibenz[b,f]oxepin-10-ylmethyl)amine are obtained in the form of a light-yellow oil; TLC (silica gel; ethyl acetate; UV): Rf =0.09.