Thiophene → 2-Aminobenzimidazole

HRID 1534726ノート

反応式

HRID 1534726 の反応式
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]

参加物

9

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 136242-Aminobenzimidazole

試薬・触媒・溶媒 3

HCID 23938Palladium触媒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 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).

後処理

  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

出典と根拠

ORDレコード
ord-555280e794774d178d0da1b678dc167c
出典データセット
uspto-grants-1992_02
特許番号
USRE033833

反応ノート

読み込み中…