Water → 4-(4-Fluorobenzoylamino)-1-(4-trifluoromethoxybenzoyl)piperidine

HRID 49785Notes

Reaction equation

HRID 49785 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.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.O>ClCCl>[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:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:26]([O:25][C:24]([F:23])([F:35])[F:36])=[CH:27][CH:28]=3)[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 1

HCID 98228134-(4-Fluorobenzoylamino)-1-(4-trifluoromethoxybenzoyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-fluorobenzoylamino)piperidine (0.15 g) in dichloromethane (5 ml) were added in turn pyridine (82 μl) and 4-trifluoromethoxybenzoyl chloride (106 μ) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 4 hours, which was taken up into a mixture of water and dichloromethane. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate, and brine, and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave 4-(4-fluorobenzoylamino)-1-(4-trifluoromethoxybenzoyl)piperidine (205 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 of the solvent under reduced pressure

Sources & evidence

ORD record
ord-12dc8b3889c647648bf71c64dcb75b6c
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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