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

HRID 979908Notes

Reaction equation

HRID 979908 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 was stirred and refluxed for 8 hours. The reaction mixture was evaporated and the residue was taken up in water. The whole was alkalized with ammonium hydroxide and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane. The product was filtered off and dried, yielding 7 parts (28%) of ethyl 4-(1H-benzimidazol-2-yl-amino)-1-piperidinecarboxylate (41).

Workup

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

Sources & evidence

ORD record
ord-4fe24f59b0234d148b446927ac153bfa
Source dataset
uspto-grants-1987_01
Patent number
US04634704

Reaction notes

Loading…