Potassium Carbonate → 2,4-Bis(trifluoromethyl)benzamide

HRID 1950900

반응식

HRID 1950900 반응식
N[C@H]1CCCC[C@H]1[NH:8][C:9](=[O:26])[C:10]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:12][C:11]=1OC.C(=O)([O-])[O-].[K+].[K+].[I-].C([N+]1(C)CCC(=O)CC1)C>C(O)C>[F:21][C:20]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([C:16]([F:19])([F:17])[F:18])[C:10]([C:9]([NH2:8])=[O:26])=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 58062915cis-N-(2-Amino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide2회

생성물 1

HCID 27360992,4-Bis(trifluoromethyl)benzamide수율 120%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

cis-N-(2-Amino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide (intermediate H) (400 mg, 1.04 mmol) was dissolved in 27 mL ethanol. Potassium carbonate (86 mg, 0.062 mmol) and 1-ethyl-1-methyl-4-oxo-piperidinium iodide (420 mg, 1.56 mmol) were added. The reaction mixture was refluxed for 2 h. The solvent was evaporated off. The residue was extracted with saturated sodium bicarbonate solution and ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/ethyl acetate 1:0->1:1) yielded cis 2-methoxy-N-2-(4-oxo-piperidin-1-yl)-cyclohexyl]-4,6-bis-trifluoromethyl-benzamide as a light yellow solid (321 mg, 66%), MS: m/e=467.2 [(M+H)+].

후처리

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customThe solvent was evaporated off
  3. extractionThe residue was extracted with saturated sodium bicarbonate solution and ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/ethyl acetate 1:0->1:1)

출처 및 근거

ORD 기록
ord-2fc3b3e3aa674781b526b6bf02b76ee4
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404673B2

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