Acetic Anhydride → HCID 18381944, compound

HRID 2297517Notes

Reaction equation

HRID 2297517 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)O)[CH2:5]1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>[C].[Pd].CO>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 18381931HCID 18381931, compound

Product 1

HCID 18381944HCID 18381944, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

To 1-acetyl-3-(diphenylhydroxymethyl)piperidine (500 mg), acetic anhydride (2 ml) was added and the mixture was stirred at 140° C. for 16 hours. After concentration of the reaction solution, 10 ml of methanol and 30 mg of 10% palladium-carbon were added, followed by stirring the mixture under hydrogen atmosphere for 17 hours. Palladium was removed by filtration through Celite and the filtrate was concentrated to obtain 250 mg of 1-acetyl-3-(diphenylmethyl)piperidine. Yield: 52%.

Workup

  1. stirringby stirring the mixture under hydrogen atmosphere for 17 hours
  2. customPalladium was removed by filtration through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b78ef75ecd0f4d1799b68e9dc6eca380
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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