Pyridine → 1-[1-(4-Butyl-benzoyl)-piperidin-4-yl]-5-fluoro-1,3-dihydro-benzoimidazol-2-one

HRID 1295766Notes

Reaction equation

HRID 1295766 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH2:24]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:24]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([N:13]2[CH2:12][CH2:11][CH:10]([N:6]3[C:5]4[CH:16]=[CH:17][C:2]([F:1])=[CH:3][C:4]=4[NH:8][C:7]3=[O:9])[CH2:15][CH2:14]2)=[O:33])=[CH:35][CH:36]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1200494-Butylbenzoyl chlorideHCID 137921045-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 692399051-[1-(4-Butyl-benzoyl)-piperidin-4-yl]-5-fluoro-1,3-dihydro-benzoimidazol-2-oneYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-fluoro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (29.4 mg, 0.125 mmol) in methylene chloride (1 mL) was added pyridine (0.12 μL, 0.15 mmol) and 4-n-butylbenzoyl chloride (26 μL, 0.138 mmol). The reaction mixture was stirred overnight 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 to give 1-[1-(4-butyl-benzoyl)-piperidin-4-yl]-5-fluoro-1,3-dihydro-benzoimidazol-2-one (6.1 mg; 12%) was obtained as a glass.

Workup

  1. customthen purified directly by column chromatography on silica gel
  2. washby eluting with methylene chloride
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78a59c303ef14456ac89a6c8c38771d0
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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