Triethylamine → 1-[1-(3-chloro-3-phenylpropyl)piperidin-4-yl]-5-(methylsulfonyl)-1H-benzimidazole

HRID 1434592Notes

Reaction equation

HRID 1434592 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][S:7]([C:10]1[CH:34]=[CH:33][C:13]2[N:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)O)[CH2:19][CH2:18]3)[CH:15]=[N:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8].C(N(CC)CC)C>ClCCl>[Cl:5][CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][CH:17]([N:14]2[C:13]3[CH:33]=[CH:34][C:10]([S:7]([CH3:6])(=[O:9])=[O:8])=[CH:11][C:12]=3[N:16]=[CH:15]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68704632HCID 68704632, compound

Product 1

HCID 579360111-[1-(3-chloro-3-phenylpropyl)piperidin-4-yl]-5-(methylsulfonyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.46 ml) was added to a solution of 3-{4-[5-(methylsulfonyl)-1H-benzimidazol-1-yl]piperidin-1-yl}-1-phenylpropan-1-ol (2.1 g) and triethylamine (0.9 ml) in dichloromethane (30 ml) at 0° C. The mixture was allowed to warm to room temperature and stirring was continued for 16 hours. The reaction mixture was washed with water (15 ml) and brine (15 ml) and dried. Removal of the solvent gave the title compound as an orange foam, yield 1.85 g, M+H 432.

Workup

  1. washThe reaction mixture was washed with water (15 ml) and brine (15 ml)
  2. customdried
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-bcbab8cc4ebf4c97bbb1eab318b4c20c
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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