Thiophene → 2-Aminobenzimidazole

HRID 1534726

반응식

HRID 1534726 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

HCID 136242-Aminobenzimidazole

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 80192-Methoxyethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-555280e794774d178d0da1b678dc167c
출처 데이터셋
uspto-grants-1992_02
특허 번호
USRE033833

연결된 노트

불러오는 중…