Potassium Iodide → N-[1-[2-(ethenyloxy)ethyl]-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

HRID 280338

反応式

HRID 280338 の反応式
Cl[CH2:2][CH2:3][O:4][CH:5]=[CH2:6].Br.Br.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH:5]([O:4][CH2:3][CH2:2][N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:18]2[N:17]([CH2:16][C:13]3[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=2)[CH2:28][CH2:29]1)=[CH2:6]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 80742-Chloroethyl vinyl etherHCID 10340Sodium CarbonateHCID 3018631Norastemizole hydrobromide

生成物 1

HCID 13653865N-[1-[2-(ethenyloxy)ethyl]-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine収率 32%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1.6 parts of 1-chloro-2-(ethenyloxy)ethane, 7.3 parts of 1-(4-fluorophenylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 3.1 parts of sodium carbonate, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 70° C. The reaction mixture was poured onto water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1.9 parts (32%) of N-[1-[2-(ethenyloxy)ethyl]-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine; mp. 138.5° C. (compound 1).

後処理

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted with 4-methyl-2-pentanone
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from acetonitrile

出典と根拠

ORDレコード
ord-eec8b0d9934e41c8810236d0bc8d8b24
出典データセット
uspto-grants-1986_05
特許番号
US04588722

関連ノート

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