2-Chlorobenzimidazole → 1-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl ester

HRID 1070490Notes

Reaction equation

HRID 1070490 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>CN1CCCC1=O>[NH:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=[C:2]1[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-chlorobenzimidazole (1 g) and ethyl 4-amino-1-piperidinecarboxylate (2 g) in 1-methyl-2-pyrrolidinone was heated at 130° C. for 24 h. The mixture was partitioned between water and ethyl acetate, the organic layer washed with water, dried and evaporated under reduced pressure. Purification was by chromatography eluting with 1% triethylamine/5% methanol in dichloromethane. Yield 0.630 g as a solid.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic layer washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 1% triethylamine/5% methanol in dichloromethane

Sources & evidence

ORD record
ord-58e2f97242be4da8946c18e80175f48d
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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