Dimethylformamide → 4-(1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin4-yl)butyric acid ethyl ester

HRID 1108211Notes

Reaction equation

HRID 1108211 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[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[NH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1C=CC=CC=1>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH:23]1[CH2:24][CH2:25][N:20]([CH2:2][CH2:3][CH:4]=[C:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]2=3)[CH2:21][CH2:22]1)[CH3:33]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 17126855-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 106318484-Piperidinebutanoic acid, ethyl ester

Product 1

HCID 540820164-(1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin4-yl)butyric acid ethyl esterYield 83%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (5.8 g, 19.8 mmol), ethyl 4(piperidin-4-yl)butyrate (6.1 g, 29 mmol), potassium carbonate (2.9 g, 21 mmol) and N,N-dimethylformamide (10 ml) was heated at 120° C. for 5 h. After cooling, benzene (50 ml) and water (50 ml) were added and the phases were separated. The organic phase was dried and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel (50 g) using mixtures of benzene and chloroform as eluents to give 6.9 g (83%) of 4-(1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)butyric acid ethyl ester as an oil.

Workup

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

Sources & evidence

ORD record
ord-32e70cec35cc439b91cb9176bb80f848
Source dataset
uspto-grants-2000_05
Patent number
US06066632

Reaction notes

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