Water → HCID 22329013, compound

HRID 587061Notes

Reaction equation

HRID 587061 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].N1C=CC=CC=1.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38].O>C1COCC1.CN(C)C1C=CN=CC=1>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:23][CH2:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22328987methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 22329013HCID 22329013, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In THF (11.2 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate (0.56 g). To the solution were added pyridine (0.17 ml) and ethyl chloroformate (0.18 ml, and the mixture was stirred at room temperature for 3 hours. To the mixture was added 4-dimethylaminopyridine (169 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 7-[4-(2-butoxyethoxy)phenyl]-1-(ethoxycarbonyl)-2,3-dihydro-1-benzazepine-4-carboxylate (580 mg).

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-8ad53524a5314fd4964abad49fed50e0
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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