1-Benzyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)piperidine → N-(piperidin-4-yl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

HRID 494402

반응식

HRID 494402 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>O1CCCC1CO.[OH-].[Pd+2].[OH-]>[NH3:8].[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([C:18]2[C:17]([C:15]([NH:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:16])=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:28][CH:27]=1

참가 물질

5

반응물 1

HCID 229956921-Benzyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)piperidine

생성물 2

HCID 222AmmoniaHCID 9928271N-(piperidin-4-yl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide수율 176.4%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매2회HCID 7360Tetrahydrofurfuryl alcohol용매

실험 절차

To a solution of the 1-benzyl-4-(4′-trifluoromethylbiphenyl-2-carbonylamino)piperidine (1.47 g) obtained in Example 8a) in tetrahydrofuran-methanol (1:1; 50 mL) was added palladium hydroxide (300 mg) in a stream of argon under ice-cooling. The mixture was stirred for one day at normal pressure under hydrogen atmosphere, and further stirred for one day at normal pressure under hydrogen atmosphere after further addition of palladium hydroxide (300 mg). The reaction mixture was filtered through a Celite pad and washed with methanol. The filtrate and the washings were combined, concentrated in vacuo and purified by column chromatography on silica gel with chloroform:methanol:aqueous ammonia=100:10:1 to give the title compound (1.03 g).

후처리

  1. temperaturecooling
  2. stirringfurther stirred for one day at normal pressure under hydrogen atmosphere
  3. filtrationThe reaction mixture was filtered through a Celite pad
  4. washwashed with methanol
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on silica gel with chloroform

출처 및 근거

ORD 기록
ord-acf22412513b4430899df264ef800621
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538140B2

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