Dichloromethane → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[3-(1-methyl-1H-imidazol-4-yl)propyl]piperazine dihydrochloride

HRID 584183노트

반응식

HRID 584183 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].[CH3:32][N:33]1[CH:37]=[C:36]([CH2:38][CH2:39][CH:40]=O)[N:35]=[CH:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].[Cl:61]CCl>>[ClH:61].[ClH:61].[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:40][CH2:39][CH2:38][C:36]2[N:35]=[CH:34][N:33]([CH3:32])[CH:37]=2)[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

참가 물질

6

반응물 5

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 223429433-(1-methyl-1H-imidazol-4-yl)propanalHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

생성물 1

HCID 86588508(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[3-(1-methyl-1H-imidazol-4-yl)propyl]piperazine dihydrochloride

실험 절차

Under nitrogen atmosphere, to a mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (315 mg) and 3-(1-methyl-1H-imidazol-4-yl)propanal (98 mg) in dichloromethane (6 ml) was added sodium triacetoxyborohydride (225 mg) and'stirred at room temperature. After 4 hours, aqueous sodium bicarbonate solution was added to the mixture and the mixture was stirred for several minutes. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using dichloromethanemethanol (10:1) as eluent and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[3-(1-methyl-1H-imidazol-4-yl)propyl]piperazine dihydrochloride (187.1 mg).

후처리

  1. customat room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel using dichloromethanemethanol (10:1) as eluent
  6. additiontreated with 4N hydrogen chloride in ethyl acetate solution

출처 및 근거

ORD 기록
ord-75d8ebf8014f41d2965923c941025e00
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924278B2

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