Triethylamine → 1-Tritylpiperidin-4-one

HRID 397605Notes

Reaction equation

HRID 397605 reaction equation
C.Cl[C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.O.[NH:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1.C(N(CC)CC)C>CN(C)C=O>[C:4]1([C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:24]2[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723901PiperonylamineHCID 70032815Chlorotriphenylmethane methane

Product 1

HCID 27484141-Tritylpiperidin-4-oneYield 103.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After the portionwise addition of 18.1 g (65.1 mmol) of chlorotriphenylmethane methane to a 150 ml dimethylformamide solution of 10.0 g (65.1 mmol) of 4-piperidone monohydrate hydrochloride and 20.0 g (198 mmol) of triethylamine at 60° C. under stirring, the resulting mixture was stirring further for 5 hours at the same temperature. The triethylamine hydrochloride precipitated by cooling was filtered out and the filtrate was concentrated under reduced pressure. To the residue was added 150 ml of water, followed by extraction with 300 ml of ethyl acetate. The organic layer was then washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, whereby 23.0 g (yield: 98.3%) of 1-triphenylmethyl-4-piperidone were obtained.

Workup

  1. stirringthe resulting mixture was stirring further for 5 hours at the same temperature
  2. customThe triethylamine hydrochloride precipitated
  3. temperatureby cooling
  4. filtrationwas filtered out
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue was added 150 ml of water
  7. extractionfollowed by extraction with 300 ml of ethyl acetate
  8. washThe organic layer was then washed with saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5102503fe3a4a0fb04bc62843922f07
Source dataset
uspto-grants-2003_08
Patent number
US06610708B1

Reaction notes

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