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

HRID 584183ノート

反応式

HRID 584183 の反応式
[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]

参加物

6

反応物 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

生成物 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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-75d8ebf8014f41d2965923c941025e00
出典データセット
uspto-grants-2005_08
特許番号
US06924278B2

反応ノート

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