Trityl chloride → 1-Tritylpiperidin-4-one

HRID 2288030Notes

Reaction equation

HRID 2288030 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[C:19]1([C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2723901Piperonylamine

Product 1

HCID 27484141-Tritylpiperidin-4-oneYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.6 g (65.1 mmol) of 4-piperidone monohydrate hydrochloride and 20.0 g (198 mmol) of triethylamine in 150 ml of dimethylformamide, 18.1 g (65.1 mmol) of chlorotriphenylmethane were added at 60° C. in portions under stirring, followed by stirring for further 5 hours at the same temperature. After cooling, the triethylamine hydrochloride thus precipitated was filtered off and the filtrate was concentrated by evaporation under reduced pressure. To the residue, 150 ml of water were added and the resulting mixture was extracted with 300 ml of ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was concentrated by evaporation under reduced pressure, whereby 23.0 g (yield: 98.3%) of 1-triphenylmethyl-4-piperidone were obtained.

Workup

  1. stirringby stirring for further 5 hours at the same temperature
  2. temperatureAfter cooling
  3. customthe triethylamine hydrochloride thus precipitated
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  6. additionTo the residue, 150 ml of water were added
  7. extractionthe resulting mixture was extracted with 300 ml of ethyl acetate
  8. washThe organic layer was washed with saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe solvent was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-046d39004f6e4da8b0ce78369f5c4f0a
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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