Formic Acid → 1-{1-[3-(6-chloro-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 46910Notes

Reaction equation

HRID 46910 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[NH:21][C:20]2=[O:28])[CH2:15][CH2:14]1.Cl.[CH:30](O)=O>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[CH:30][N:9]([CH2:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH:16]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:17][CH2:18]3)[C:3]=2[CH:4]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 20385565HCID 20385565, compound

Product 1

HCID 203856141-{1-[3-(6-chloro-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-oneYield 27%

Procedure

A mixture of 4 parts of 1-[1-{3-[N-(2-amino-5-chlorophenyl)amino]propyl}-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one, 6 parts of a concentrated hydrochloric acid solution and 30 parts of formic acid is stirred and refluxed overnight. The reaction mixture is evaporated and water is added to the residue. The whole is alkalized with a diluted ammonium hydroxide solution and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and recrystallized from 2-propanol, yielding 1.1 parts (27%) of 1-{1-[3-(6-chloro-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 214.9° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. additionwater is added to the residue
  4. extractionthe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 4-methyl-2-pentanone
  9. filtrationThe product is filtered off
  10. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-5967259dd5354166978afa5a01b86e2f
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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