2-Chlorobenzimidazole → N-(1-Benzylpiperidin-4-yl)-1H-benzimidazol-2-amine

HRID 582054

Reaction equation

HRID 582054 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:24][CH:21]1[CH2:22][CH2:23][N:18]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 16640950N-(1-Benzylpiperidin-4-yl)-1H-benzimidazol-2-amine

Procedure

Combine 2-chloro-1H-benzimidazole (5.0 g, 33 mmol) and 1-benzyl-4-aminopiperidine (14.2 g, 75 mmol) and heat to about 150° C. After 12 hours, cool and partition between water and chloroform, warming if necessary. Separate the layers and add methanol and toluene to the organic layer. Evaporate the organic layer in vacuo to give a solid. Triturate the solid with ethyl acetate, collect by filtration, and dry to give (1H-benzimidazol-2-yl)(1-benzylpiperidin-4-yl)amine: Rf =0.30 (2% triethylamine/10% methanol/ethyl acetate).

Workup

  1. temperaturecool
  2. custompartition between water and chloroform
  3. temperaturewarming if necessary
  4. customSeparate the layers
  5. additionadd methanol and toluene to the organic layer
  6. customEvaporate the organic layer in vacuo
  7. customto give a solid
  8. customTriturate the solid with ethyl acetate
  9. filtrationcollect by filtration
  10. customdry

Sources & evidence

ORD record
ord-d4d8e37fcd0a4bc8977bd503b9a5113f
Source dataset
uspto-grants-1999_07
Patent number
US05922737

Linked notes

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