(1,1'-Biphenyl)-4-sulphonyl chloride → 2-[1-(biphenyl-4-ylsulfonyl)piperidin-4-yl]-1H-benzimidazole

HRID 1913153Notes

Reaction equation

HRID 1913153 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[N:24]=2)[CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7]([N:17]2[CH2:18][CH2:19][CH:20]([C:23]3[NH:24][C:25]4[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=4[N:27]=3)[CH2:21][CH2:22]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 81531DiisopropylethylamineHCID 7158102-(piperidin-4-yl)-1H-1,3-benzodiazole

Product 1

HCID 445656382-[1-(biphenyl-4-ylsulfonyl)piperidin-4-yl]-1H-benzimidazoleYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-biphenylsulfonyl chloride (63 mg, 0.25 mmol) and 2-(piperidin-4-yl)-1H-benzimidazole (50 mg, 0.25 mmol) in DCM (10 mL) is added N,N-diisopropylethylamine (62 μL, 0.37 mmol). After 18 h the reaction mixture is washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Trituration with heptane gives 21 mg of 2-[1-(biphenyl-4-ylsulfonyl)piperidin-4-yl]-1H-benzimidazole.

Workup

  1. washAfter 18 h the reaction mixture is washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ad410efecb945429ec478aaaf9a3ce8
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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