Potassium Iodide → N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-1-methyl-1H-pyrrole-2-carboxamide hydrochloride hydrate

HRID 437668ノート

反応式

HRID 437668 の反応式
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:6].[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[NH:21][C:20]2=[O:28])[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+].[I-].[K+]>CC(C)CC(=O)C>[OH2:6].[ClH:1].[O:28]=[C:20]1[N:19]([CH:16]2[CH2:15][CH2:14][N:13]([CH2:2][CH2:3][NH:4][C:5]([C:7]3[N:8]([CH3:12])[CH:9]=[CH:10][CH:11]=3)=[O:6])[CH2:18][CH2:17]2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21]1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 516892Sodium BicarbonateHCID 21428944N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide

生成物 1

HCID 21428890N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-1-methyl-1H-pyrrole-2-carboxamide hydrochloride hydrate

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A mixture of 5.6 parts of N-(2-chloroethyl)-1-methyl-1H-pyrrole-2-carboxamide, 6.52 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 2.52 parts of sodium hydrogen carbonate, 0.1 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone is stirred and refluxed for 62 hours. The reaction mixture is cooled and the solvent is evaporated. The residue is purified by columnchromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the hydrochloride salt in ethanol, 2-propanol and 2,2'-oxybispropane. The salt is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 0.6 parts of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-1-methyl-1H-pyrrole-2-carboxamide hydrochloride hydrate; mp. 237.7° C.

後処理

  1. temperaturerefluxed for 62 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. customThe residue is purified by columnchromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions are collected
  7. customthe eluent is evaporated
  8. filtrationThe salt is filtered off
  9. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane

出典と根拠

ORDレコード
ord-d06e4e1cbd07450aa868c847d0848b62
出典データセット
uspto-grants-1977_06
特許番号
US04031226

反応ノート

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