Water → 1-Acetyl-4-(4-fluorophenoxycarbonylamino)piperidine

HRID 49779

Reaction equation

HRID 49779 reaction equation
Cl.[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)(=[O:4])[CH3:3].N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:20].O>ClCCl.C(OCC)(=O)C>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:20])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 27332564-Fluorophenyl chloroformateHCID 172216421-Acetyl-4-aminopiperidine hydrochloride

Product 1

HCID 98171611-Acetyl-4-(4-fluorophenoxycarbonylamino)piperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-acetyl-4-aminopiperidine hydrochloride (0.4 g) in dichloromethane (5 ml) were added in turn pyridine (0.54 ml) and 4-fluorophenyl chloroformate (0.29 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour, which was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give 1-acetyl-4-(4-fluorophenoxycarbonylamino)piperidine (347 mg).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-e12882cfc33742e9af733bf1dc0f1f80
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

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