Thiophene → 1-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine

HRID 637403

반응식

HRID 637403 반응식
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=[C:27]2[NH:35][CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:21][CH:20]=1.S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>C(O)C.COCCO>[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:28]=[C:27]2[NH:35][CH:36]2[CH2:37][CH2:38][N:39]([CH:11]3[CH2:12][CH2:13][CH2:14][N:9]([CH2:8][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:10]3)[CH2:40][CH2:41]2)=[CH:21][CH:20]=1

참가 물질

8

반응물 5

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

생성물 1

HCID 135880701-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine

시약·촉매·용매 2

HCID 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 parts 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 palldium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate 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'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine; mp. 174.6° C. (intermediate 70).

후처리

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate 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-8c3a50b0a37c4b588229f06d8f4bbcb9
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04556660

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