Sodium Hydroxide → 1-Diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine

HRID 22248

반응식

HRID 22248 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:21]1([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C(Cl)Cl.CN(C)C=O>[C:34]1([CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:28]2[CH2:29][CH2:30][N:31]([C:14]([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=4)[CH:13]=[CH:12][CH:11]=3)=[O:16])[CH2:32][CH2:33]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 70048BenzhydrylpiperazineHCID 27739784'-Methyl-biphenyl-3-carboxylic acid

생성물 1

HCID 194302781-Diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine수율 82.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매3회

실험 절차

To a suspension of 4'-methylbiphenyl-3-carboxylic acid (2.2 g) in a mixture of methylene chloride (20 ml) and dimethylformamide (0.5 ml) was added thionyl chloride (1.48 g). The mixture was refluxed until the suspension dissolved, after which the temperature was allowed to cool to room temperature. To this solution was added 1-(diphenylmethyl)piperazine (3.94 g) in methylene chloride dropwise, and the reaction mixture allowed to stand overnight. Sodium hydroxide (30 ml of 1N) and 50 ml of methylene chloride was added, the organic layer separated, washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 25% ethyl acetate in heptane, to yield 3.8 g of 1-diphenylmethyl-4-(4'-methylbiphenyl-3-carbonyl)piperazine. The dihydrochloride salt was prepared and recrystallized from ethanol, m.p. 226° C.

후처리

  1. temperatureThe mixture was refluxed until the suspension
  2. dissolutiondissolved
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 25% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-e481b8e584144ef89b2fb87ecd0fa678
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428037

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