Water → 4-(4-Fluorobenzoylamino)-1-methoxycarbonylpiperidine

HRID 49784Notes

Reaction equation

HRID 49784 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:24]([O:26][CH3:27])=[O:25].O>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:24]([O:26][CH3:27])=[O:25])[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 1

HCID 99256834-(4-Fluorobenzoylamino)-1-methoxycarbonylpiperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-fluorobenzoylamino)piperidine (0.25 g) in dichloromethane (5 ml) were added in turn pyridine (0.14 ml) and methyl chloroformate (87 μl) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour. To the mixture was added N,N-dimethylaminopyridine (0.13 g) and allowed to stir for another 1 hour. The reaction mixture 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 4-(4-fluorobenzoylamino)-1-methoxycarbonylpiperidine (0.265 g).

Workup

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

Sources & evidence

ORD record
ord-8fc580b69f654dc09dbfd4998ccc95cd
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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