Water → 1-(1-Benzyl-4-methyl-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one

HRID 239118Notes

Reaction equation

HRID 239118 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:15][C:16]2[C:17]([NH2:22])=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1.O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([N:15]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22][C:28]2=[O:29])([CH3:14])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 86686490N-(1-Benzyl-4-methyl-piperidin-4-yl)-benzene-1,2-diamine

Product 1

HCID 866864921-(1-Benzyl-4-methyl-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-oneYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 121 mg N-(1-benzyl-4-methyl-piperidin-4-yl)-benzene-1,2-diamine and 79 mg CDI in 5 mL dichlormethane was stirred 24 h at RT. Water was added and the mixture was extracted with ethylacetate. The organic layer was concentrated to give 119 mg of the desired product. (M+H)+:322

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-3f21ef66e779473999e289c4e9719cdd
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

Loading…