Pyridine → HCID 16457793, compound

HRID 1295763Notes

Reaction equation

HRID 1295763 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]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:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C:5]4[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)=[O:32])=[CH:34][CH:35]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 1200494-Butylbenzoyl chloride

Product 1

HCID 16457793HCID 16457793, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-keto-1-benzimidazolinyl)piperidine (0.34 g, 1.57 mmol) in methylene chloride (8 mL) was added pyridine (0.15 mL, 1.88 mmol) and 4-n-butylbenzoyl chloride (0.37 g, 1.88 mmol). The reaction mixture was stirred for 1 h then purified directly by column chromatography on silica gel by eluting with methylene chloride followed by ethyl acetate. The product fractions were combined and concentrated in vacuo. The residue was triturated with ethyl ether and the solids collected by filtration and rinsed with hexanes. 1-[1-(4-Butyl-benzoyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one (0.48 g; 81%) was obtained as white solid.

Workup

  1. customthen purified directly by column chromatography on silica gel
  2. washby eluting with methylene chloride
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with ethyl ether
  5. filtrationthe solids collected by filtration
  6. washrinsed with hexanes

Sources & evidence

ORD record
ord-f014f1a645c54123b871c7f1e8464f37
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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