Borane → 4-Benzenesulfonyl-2-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazine

HRID 560120Notes

Reaction equation

HRID 560120 reaction equation
B.[C:2]1([S:8]([N:11]2[CH2:16][CH:15]([C:17]3[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[N:14]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:13](=O)[CH2:12]2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OP([O-])(O)=O.[K+].C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[C:2]1([S:8]([N:11]2[CH2:12][CH2:13][N:14]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:15]([C:17]3[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:16]2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6331BoraneHCID 516892Sodium BicarbonateHCID 516951Monobasic potassium phosphateHCID 445485594-Benzenesulfonyl-6-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-one

Product 1

HCID 445485604-Benzenesulfonyl-2-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazineYield 29%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A solution of borane in THF (1M, 274.4 μL) was added to a solution of 4-benzenesulfonyl-6-(3′-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-one (50 mg) in THF (1.5 mL). The reaction mixture was heated to 85° C. for 3 hours. An aqueous solution of KH2PO4 (1M, 2 mL) was added slowly and the biphasic mixture was heated to 75° C. for 15 min, and then poured into a saturated solution of sodium bicarbonate. Ethyl acetate was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×2). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 1:1) yielded 4-benzenesulfonyl-2-(3′-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazine (14 mg, 29%) as a white foam, MS: 533.3 (M+H)+.

Workup

  1. temperaturethe biphasic mixture was heated to 75° C. for 15 min
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with ethyl acetate (×2)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8a3fcc5827a419dbe839ecffb372d7f
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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