Ethyl Acrylate → Ethyl 3-[N-[3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]propionate

HRID 1647435Notes

Reaction equation

HRID 1647435 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.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>C(O)C>[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]([CH2:23][CH2:22][C:21]([O:25][CH2:26][CH3:27])=[O:24])[CH3:1])[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 9918Norcyclobenzaprine

Product 1

HCID 15291884Ethyl 3-[N-[3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.61 g of 5-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene, 1.20 g of ethyl acrylate, and 13 ml of ethanol was refluxed for 2 hours. After reaction was completed, the solvent was removed by distillation and the residue was purified by column chromatography on aluminum oxide [n-hexane-diethyl ether (1:1)] to give 3.22 g of slightly yellow viscous liquid.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter reaction
  3. customthe solvent was removed by distillation
  4. customthe residue was purified by column chromatography on aluminum oxide [n-hexane-diethyl ether (1:1)]
  5. customto give 3.22 g of slightly yellow viscous liquid

Sources & evidence

ORD record
ord-2c4494bf6ceb4526bd76527c5f8f299d
Source dataset
uspto-grants-1995_07
Patent number
US05432192

Reaction notes

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