Water → Methyl 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587062Notes

Reaction equation

HRID 587062 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[NH:24][CH2:23][CH2:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].Cl[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32].O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:34]([O:33][C:31]([N:24]1[C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][CH:13]=3)=[CH:29][C:19]=2[CH:20]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:22][CH2:23]1)=[O:32])[CH:35]=[CH2:36]

Participants

6

Reactant 3

HCID 962WaterHCID 18052Allyl chloroformateHCID 22328987methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22328895Methyl 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In pyridine (4.3 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate (0.43 g). To the solution was added allyl chloroformate (0.23 ml), and the mixture was stirred at room temperature for 14 hours. To the mixture was added 4-dimethylaminopyridine (40 mg), and the mixture was stirred at room temperature for 2 hours. The reaction solution was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate→3/1) to give methyl 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate (0.30 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate→3/1)

Sources & evidence

ORD record
ord-4d0ab89b2b0f4d19a79f50693d558a67
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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