Acetyl chloride → HCID 42611207, compound

HRID 1260933Notes

Reaction equation

HRID 1260933 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@H:15]([N:16]([CH3:33])[C:17](=[O:32])[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[CH2:14][CH2:13][N:12]([C:34]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[O:35])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(CC)CC)C.[C:49](Cl)(=[O:51])[CH3:50].[OH-].[Na+]>C(#N)C.O>[C:49]([N:39]1[CH2:40][CH2:41][CH:36]([C:34]([N:12]2[CH2:13][CH2:14][C@@H:15]([N:16]([CH3:33])[C:17](=[O:32])[C:18]3[CH:23]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:21]=[C:20]([C:28]([F:29])([F:31])[F:30])[CH:19]=3)[C@H:10]([C:5]3[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=3)[CH2:11]2)=[O:35])[CH2:37][CH2:38]1)(=[O:51])[CH3:50]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 86631339N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylcarbonyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide Monohydrochloride

Product 1

HCID 42611207HCID 42611207, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-[(3R,4R)-3-(3,4-dichlorophenyl)-1-(piperidin-4-ylcarbonyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide monohydrochloride (0.35 g) obtained in Example 89 and triethylamine (0.24 mL) in acetonitrile (10 mL) was added acetyl chloride (0.080 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, the mixture was made basic with 2N aqueous sodium hydroxide solution, and the resultant product was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 75→100% ethyl acetate/hexane) to give the title compound (0.25 g, 71%) as a white crystal powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 75→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-412b4328d9ca458e98fabdb7eaa19278
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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