3,5-Dimethylbenzoyl Chloride → HCID 22851570, compound

HRID 264606Notes

Reaction equation

HRID 264606 reaction equation
C(=O)(O)[O-].[Na+].[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([CH3:16])[CH:15]=1)[C:10](Cl)=[O:11].FC(F)(F)C(O)=O.[CH2:24]([C@@H:31]1[CH2:36][CH:35]([NH:37][C:38](=[O:43])[C:39]([F:42])([F:41])[F:40])[CH2:34][CH2:33][NH:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.O>[CH2:24]([C@@H:31]1[CH2:36][CH:35]([NH:37][C:38](=[O:43])[C:39]([F:42])([F:40])[F:41])[CH2:34][CH2:33][N:32]1[C:10](=[O:11])[C:9]1[CH:8]=[C:7]([CH3:6])[CH:15]=[C:14]([CH3:16])[CH:13]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 810883,5-Dimethylbenzoyl ChlorideHCID 516892Sodium BicarbonateHCID 22851571HCID 22851571, compound

Product 1

HCID 22851570HCID 22851570, compound

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

710 mg of solid sodium bicarbonate and 712 mg of 3,5-dimethylbenzoyl chloride are added to a stirred mixture of 1.39 g (3.44 mmol) of (2R,4RS)-N-(2-benzyl-4-piperidyl)trifiuoroacetamide trifluoroacetate and 10 ml of toluene/water (1:1) cooled in ice-water. The reaction mixture is then allowed to warm to room temperature, subsequently stirred for 2 hours and partitioned between toluene and 1N sodium bicarbonate solution. The organic phases are washed with water, dried over magnesium sulfate and evaporated to dryness. The colourless oil is chromatographed on silica gel with ethyl acetate/hexane 1:2, resulting in the title compound. This is used further without further purification.

Workup

  1. custompartitioned between toluene and 1N sodium bicarbonate solution
  2. washThe organic phases are washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe colourless oil is chromatographed on silica gel with ethyl acetate/hexane 1:2

Sources & evidence

ORD record
ord-6bdbd33602e54d9eabca79dd3073282d
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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