Dimethylformamide → 1-(3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-cyclohexyl4-piperidinecarboxylic acid ethyl ester

HRID 1004085Notes

Reaction equation

HRID 1004085 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[CH:20]1([C:26]2([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC=CC=1>[CH2:35]([O:34][C:32]([C:26]1([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH:4]=[C:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH:9]=[CH:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH2:30][CH2:31]1)=[O:33])[CH3:36]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18418945Ethyl 4-cyclohexyl-4-piperidinecarboxylateHCID 229989845-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 536588481-(3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-cyclohexyl4-piperidinecarboxylic acid ethyl esterYield 39%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 5-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene (4.45 g, 14.2 mmol), ethyl 4-cyclohexyl-4-piperidinecarboxylate (3.4 g, 14.2 mmol, prepared similarly as described in Brit. 1 124 661 (1967)), potassium carbonate (2.1 g, 15.2 mmol) and N,N-dimethylformamide (10 ml) was heated at 120° C. for 5 h. Benzene (50 ml) and water (50 ml) were added and the phases were separated. The organic phase was dried and the solvent evaporated in vacuo. The residue was purified by chromatography on silica gel (50 g) using mixtures of benzene and chloroform as eluents to give 2.6 g (39%) of 1-(3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-cyclohexyl4-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. customprepared similarly
  2. customthe phases were separated
  3. customThe organic phase was dried
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-0766201d4d6f45f481452348e64d5e4a
Source dataset
uspto-grants-2000_04
Patent number
US06048856

Reaction notes

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