Ammonia → 4-Chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 1271460Notes

Reaction equation

HRID 1271460 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N>ClCCl.CO>[Cl:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18444266HCID 18444266, compound

Product 1

HCID 214934324-Chloro-1-(piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-(4-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate from Step B (2.17 g, <6.17 mmol) was dissolved in dichloromethane (10 mL) and trifluoacetic acid (5 mL) was added at room temperature. After 5 h, additional trifluoacetic acid (5 mL) was added and the reaction stirred overnight. To this solution was added 2.0 M ammonia in methanol, the mixture was filtered and the volatiles removed in vacuo. The crude product was purified by chromatography (silica gel, 1 to 25% methanol containing 1% NH3 in methylene chloride gradient elution), which gave the title compound (1.12 g). MS 352.2 (M+1).

Workup

  1. filtrationthe mixture was filtered
  2. customthe volatiles removed in vacuo
  3. customThe crude product was purified by chromatography (silica gel, 1 to 25% methanol containing 1% NH3 in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-e3e24912005b4b1bb64f813187d86abf
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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