2-Chloroethanol → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-3-(2-hydroxyethylthio)propionamide

HRID 52056ノート

反応式

HRID 52056 の反応式
[H-].[Na+].[N:3]1([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][NH:21][C:22](=[O:26])[CH2:23][CH2:24][SH:25])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:27](Cl)[CH2:28][OH:29]>CN(C)C=O>[N:3]1([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][NH:21][C:22](=[O:26])[CH2:23][CH2:24][S:25][CH2:27][CH2:28][OH:29])[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

5

反応物 3

HCID 342-ChloroethanolHCID 24758Sodium hydrideHCID 86750621N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]3-(mercapto)propionamide

生成物 1

HCID 67725561N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-3-(2-hydroxyethylthio)propionamide収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

105 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling and in an atmosphere of nitrogen, to a solution of 0.76 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-3-mercaptopropionamide (prepared as described in Preparation 3) in 24 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, 0.16 ml of ethylene chlorohydrin were added to the reaction mixture, whilst ice-cooling. The reaction mixture was stirred at room temperature for 15 minutes, after which it was poured into ice-water and extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the residue thus obtained was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and methylene chloride as the eluent, to give 0.56 g of the title compound as an oil in a 65% yield.

後処理

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 15 minutes
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated by evaporation under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by column chromatography through silica gel
  7. additionby volume mixture of methanol and methylene chloride as the eluent

出典と根拠

ORDレコード
ord-a6cd11c93742421c8b780145cc125c38
出典データセット
uspto-grants-1997_04
特許番号
US05616579

反応ノート

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