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

HRID 323179

Reaction equation

HRID 323179 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-560697a9c71444b5a7705a1b92fc2c32
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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