Water → methyl 1-benzyl-7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586923Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([N:11]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:16][C:6]=2[CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:10]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 45 °C

Procedure

In DMF (3 ml) was dissolved methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g), and the solution was added dropwise to a suspension of 60% sodium hydride (0.05 g) in DMF (1 ml) under ice-cooling. The mixture was stirred under nitrogen atmosphere for 10 minutes. Benzyl bromide (0.15 ml) was added thereto, and the mixture was heated at 45° C. for 4 hours. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-benzyl-7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g) as yellow oil.

Workup

temperaturecooling
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated
customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-625f389470204eb499acabf1164a22ac
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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