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

HRID 2195648Notes

Reaction equation

HRID 2195648 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.ClCCl.[N:23]1([C:29]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:30]=2[NH2:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>O>[N:23]1([C:29]2[CH:35]=[CH:34][C:33]([C:36]([F:38])([F:39])[F:37])=[CH:32][C:30]=2[NH:31][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 6947562-(Piperidin-1-yl)-5-(trifluoromethyl)aniline

Product 1

HCID 14224174-nitro-N-[2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitrobenzoyl chloride (64.2 mg, 0.345 mmol, commercially available product) and triethylamine (120 μl, 0.859 mmol) were sequentially added at 0° C. to a dichloromethane (2 ml) solution of 2-(1-piperidinyl)-5-(trifluoromethyl)aniline (51.2 mg, 0.209 mmol), obtained as described in Referential Example 1-2. The resulting mixture was warmed to room temperature and stirred for 60 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 (30 g, hexane/ethyl acetate=8/1-6/1). Thus, N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]-4-nitrobenzamide (GIF-0345) (46.3 mg, 56.3%) was yielded as a yellow 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 (30 g, hexane/ethyl acetate=8/1-6/1)

Sources & evidence

ORD record
ord-2be15290676a409d8aef2de29776d7f3
Source dataset
uspto-grants-2012_12
Patent number
US08338362B2

Reaction notes

Loading…