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

HRID 459890Notes

Reaction equation

HRID 459890 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 5h, 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 chromatorgraphy (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 chromatorgraphy (silica gel, 1 to 25% methanol containing 1% NH3 in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-6fa98cdb71f84b57aa05f29fc2f8d558
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

Loading…