Dichloromethane → 4-methoxy-N-[2-piperidin-1-yl-5-(trifluoromethyl)phenyl]benzamide

HRID 2410290Notes

Reaction equation

HRID 2410290 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.ClCCl.[N:22]1([C:28]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:29]=2[NH2:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O>[N:22]1([C:28]2[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:31][C:29]=2[NH:30][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 6947562-(Piperidin-1-yl)-5-(trifluoromethyl)aniline

Product 1

HCID 14227974-methoxy-N-[2-piperidin-1-yl-5-(trifluoromethyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methoxybenzoyl chloride (250 mg, 1.47 mmol, commercially available product) and triethylamine (254 μl, 1.83 mmol) were sequentially added at 0° C. to a dichloromethane (4 ml) solution of 2-(1-piperidinyl)-5-(trifluoromethyl)aniline (147 mg, 0.602 mmol), obtained as described in Referential Example 1-2. The resulting mixture was warmed to room temperature and stirred for 17 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=5/1). Thus, N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]-4-methoxybenzamide (GIF-0615) (240 mg, quant.) was yielded as a colorless solid.

Workup

  1. customobtained
  2. extractionthe resulting mixture was extracted three times with ethyl acetate
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20 g, hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4eddedd2111a4c23a399966b846db34a
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

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