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

HRID 637403

反応式

HRID 637403 の反応式
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

参加物

8

反応物 5

HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 3018631Norastemizole hydrobromideHCID 30849241-Benzyl-3-piperidone hydrochloride hydrateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 80192-Methoxyethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8c3a50b0a37c4b588229f06d8f4bbcb9
出典データセット
uspto-grants-1985_12
特許番号
US04556660

関連ノート

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