Water → Methyl 1-(3-furylmethyl)-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 586995Notes

Reaction equation

HRID 586995 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[NH:23][CH2:22][CH2:21][C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][C:18]=3[CH:28]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].[O:29]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[O:29]1[CH:33]=[CH:32][C:31]([CH2:34][N:23]2[C:17]3[CH:16]=[CH:15][C:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])=[CH:9][CH:10]=4)=[CH:28][C:18]=3[CH:19]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[CH2:21][CH2:22]2)=[CH:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 103513-FuraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22328936methyl 7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 69750332Methyl 1-(3-furylmethyl)-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (300 mg) and 3-furaldehyde (378 mg) in 1,2-dichloroethane (10 ml) was added sodium triacetoxyborohydride (416 mg), and the mixture was stirred under nitrogen atmosphere at room temperature overnight. 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=3:1) to give methyl 1-(3-furylmethyl)-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (362 mg) as yellow oil.

Workup

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

Sources & evidence

ORD record
ord-a74b23a9eac04c3ca32dc4fb353bf4e2
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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