Dimethylformamide → HCID 15291885, compound

HRID 1647436Notes

Reaction equation

HRID 1647436 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:16]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=3[C:6](=[CH:5][CH2:4][CH2:3][N:2]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:1])[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 9918NorcyclobenzaprineHCID 11430Potassium Carbonate

Product 1

HCID 15291885HCID 15291885, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.61 g of 5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene, 2.00 g of ethyl bromoacetate, 1.38 g of potassium carbonate, and 13 ml of N,N-dimethylformamide was stirred at 70° C. for 4 hours. After the reaction was completed, water was added to the reaction mixture and the mixture was then extracted with diethyl ether. The ether layer was washed with water and dried, and then the solvent was removed by distillation. The residue was purified by column chromatography on aluminum oxide [n-hexane-diethyl ether (1:1)] to give 1.88 g of slightly yellow viscous liquid.

Workup

  1. extractionthe mixture was then extracted with diethyl ether
  2. washThe ether layer was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on aluminum oxide [n-hexane-diethyl ether (1:1)]
  6. customto give 1.88 g of slightly yellow viscous liquid

Sources & evidence

ORD record
ord-c3de072b58384d23a2415f690cf03b74
Source dataset
uspto-grants-1995_07
Patent number
US05432192

Reaction notes

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