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

HRID 334261

Reaction equation

HRID 334261 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-3c743b5c80814404a61aa5b078ea4c0d
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Linked notes

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