Water → 1-Benzyl-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[C]azepine
Reaction equation
[CH2:1]([CH:8]1[C:14]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:10](=O)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>O1CCCC1>[CH2:1]([CH:8]1[C:14]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.17 mmol of 1-benzyl-8-methoxy-4,5-dihydro-1H-benzo[c]azepin-3(2H)-one in tetrahydrofuran under nitrogen atmosphere was added 3.25 mmol of lithiumaluminumhydride as 1 M solution in tetrahydrofuran. The solution was heated to reflux and stirred for 1.5 h. The mixture was cooled to room temperature and water (1 ml) was carefully added. The mixture was concentrated and the residue was dissolved in ethyl acetate. The organic phase was extracted with acidified water (acidified with 1 M HCl, 4×). To the combined aqueous phase was added NaOH (50%) until basic and ethyl acetate. The suspension was filtered over celite. The residue was washed with water and ethyl acetate. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Evaporation of the solvent gave 439 mg of crude material that was purified by flash chromatography to yield 399 mg of 1-benzyl-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine (69%).