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

HRID 1856558Notes

Reaction equation

HRID 1856558 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH: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)=S.IC>C(O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[NH: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

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 20222929HCID 20222929, compound

Product 1

HCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 28 parts of ethyl 4-{[(2-aminophenyl)aminothioxomethyl]amino}-1-piperidinecarboxylate, 112 parts of iodomethane and 240 parts of ethanol is stirred and refluxed for 8 hours. The reaction mixture is evaporated and the residue is taken up in water. The whole is alkalized with ammonium hydroxide and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product is filtered off and dried, yielding 7 parts (28%) of ethyl 4-(1H-benzimidazol-2-ylamino)-1-piperidinecarboxylate.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe reaction mixture is evaporated
  3. extractionthe product is extracted with dichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from a mixture of 2-propanol and 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-3103a4171e884bc88b9cc76626fa2487
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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