Hydrochloric Acid → 1-Benzyl-4-piperazin-1-yl-1,3-dihydro-benzoimidazol-2-one hydrochloride

HRID 730557Notes

Reaction equation

HRID 730557 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[NH:21][C:20](=[O:23])[N:19]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)C.[ClH:34]>C(OCC)(=O)C>[ClH:34].[CH2:24]([N:19]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:22]=2[NH:21][C:20]1=[O:23])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 578349934-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 688152721-Benzyl-4-piperazin-1-yl-1,3-dihydro-benzoimidazol-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.112 g of 4-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 15 mL ethyl acetate with 5 mL ethanol is added 3 mL of 2M ethanolic hydrogen chloride. The resulting solution is refluxed for one hour, and on cooling, a solid precipates. The solid is filtered and dried over night under vacuum to give 82 mg of 1-benzyl-4-piperazin-1-yl-1,3-dihydro-benzoimidazol-2-one hydrochloride. MS: 309 (M+H)+.

Workup

  1. temperatureThe resulting solution is refluxed for one hour
  2. temperatureon cooling
  3. filtrationThe solid is filtered
  4. customdried over night under vacuum

Sources & evidence

ORD record
ord-8c50fd31e1a04c2eabf8a477060221b5
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

Loading…