Benzaldehyde → (E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-one

HRID 1171633Notes

Reaction equation

HRID 1171633 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC1.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH:32](=[C:10]1/[CH2:9][N:8]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:13][CH2:12][C:11]/1=[O:14])/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 31268PyrrolidineHCID 27484141-Tritylpiperidin-4-one

Product 1

HCID 68765712(E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-oneYield 74%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(triphenylmethyl)piperidin-4-one (4.22 g) in benzene (50 ml) was added pyrrolidine (1.02 ml) at room temperature, and the resulting mixture was refluxed for 3 hours. After cooling to room temperature, benzaldehyde (1.26 ml) was added to the reaction mixture, and the resulting mixture was furthermore refluxed for 2 hours. After refluxing, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3) as the eluent to afford the title compound (3.92 g, yield: 74%) as a yellow oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. temperaturethe resulting mixture was furthermore refluxed for 2 hours
  3. temperatureAfter refluxing
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2834e8323229450fa7d7f6c49b06546f
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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