Water → Methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587010Notes

Reaction equation

HRID 587010 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.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[O:18][CH3:17])[CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 86582-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22329284Methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 75.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (1.5 g) and 2-methoxybenzaldehyde (3.62 g) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (2.82 g), and the mixture was stirred under nitrogen atmosphere at room temperature for 1 day. Then, water was added to the mixture, and the mixture was extracted-with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1) to give methyl 7-bromo-1-(2-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.62 g) as yellow oil.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-976e414bd5144d8d9613caa3414d721e
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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