Pyridine → HCID 86589517, compound

HRID 1295772Notes

Reaction equation

HRID 1295772 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[S:16])[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH2:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH2:23]([C:27]1[CH:28]=[CH:29][C:30]([C:31]([N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[NH:9][C:8]3=[S:16])[CH2:5][CH2:6]2)=[O:32])=[CH:34][CH:35]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1200494-Butylbenzoyl chlorideHCID 30344491,3-Dihydro-1-piperidin-4-yl-2H-benzimidazole-2-thione

Product 1

HCID 86589517HCID 86589517, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-piperidin-4-yl-1,3-dihydro-benzoimidazole-2-thione (0.2 g, 0.84 mmol) in methylene chloride (20 mL) was treated with pyridine (0.040 mL, 0.497 mmol) and 4-n-butylbenzoyl chloride (0.093 mL, 0.497 mmol). The reaction mixture was stirred for 18 h then purified directly by column chromatography on silica gel using ethyl acetate as the eluent to give (4-butyl-phenyl)-[4-(2-thioxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-methanone (0.167 g; 86%).

Workup

  1. customthen purified directly by column chromatography on silica gel

Sources & evidence

ORD record
ord-6a19927ad2de4f0682fea098036f70df
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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