Thiophene → 2-Aminobenzimidazole

HRID 1534726Notes

Reaction equation

HRID 1534726 reaction equation
Cl.C1(CN2CCCC(=O)C2)C=CC=CC=1.Br.Br.FC1C=CC(C[N:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=[C:27]2[NH:35]C2CCNCC2)=CC=1.S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>C(O)C.[Pd].COCCO>[NH:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[NH2:35]

Participants

9

Reactant 5

HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 3018631Norastemizole hydrobromideHCID 30849241-Benzyl-3-piperidone hydrochloride hydrateHCID 178418361HCID 178418361, compound

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 25 parts of 1(phenylmethyl)-3-piperidinone hydrochloride, 55 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 1 part of a solution of thiophene in ethanol 4%, 50 parts of potassium acetate and 500 parts of 2-methoxyethanol was hydrogenated at normal pressure and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filrate was evaporated. The residue was taken up in water and the whole was alkalized with sodium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized twice from acetonitrile. The product was filtered off and dried, yielding 9.75 parts of 1-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-bipiperidin]-4yl[-1H-benzimidazol-2-amine; mp. 174.6° C. (intermediate 70).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filrate was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized twice from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-555280e794774d178d0da1b678dc167c
Source dataset
uspto-grants-1992_02
Patent number
USRE033833

Reaction notes

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