1-Phenylpiperazine → 1-(Biphenyl-2-ylmethyl)-4-phenylpiperazine

HRID 334261

반응식

HRID 334261 반응식
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([CH:19]=O)=[CH:15][CH:16]=[CH:17][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.ClCCl.C([O-])(O)=O.[Na+]>[C:13]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

참가 물질

7

반응물 3

HCID 70961-PhenylpiperazineHCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 716025231-(Biphenyl-2-ylmethyl)-4-phenylpiperazine수율 18.3%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

1-Phenylpiperazine (266 mg, 1.64 mmol) was dissolved in methanol (7 mL) in a reaction vessel and, after adding biphenyl-2-carbaldehyde (150 mg, 0.82 mmol), the mixture was stirred at room temperature for 2 hours. 2 hours later, NaBH(OAc)3 (529 mg, 2.46 mmol) was added and the mixture was further stirred for 8 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane and saturated NaHCO3 solution was added. After extraction, organic layer was dried with anhydrous MgSO4 and then filtered. The filtrate was concentrated and the concentrate was purified by column chromatography (hexane:diethyl ether=8:1) to obtain 50 mg of the target compound (0.15 mmol, 18.3%).

후처리

  1. stirringthe mixture was further stirred for 8 hours
  2. additionwas added
  3. extractionAfter extraction, organic layer
  4. dry with materialwas dried with anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe concentrate was purified by column chromatography (hexane:diethyl ether=8:1)

출처 및 근거

ORD 기록
ord-3c743b5c80814404a61aa5b078ea4c0d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883796B2

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