Water → N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(3-hydroxypropylthio)acetamide

HRID 52110

반응식

HRID 52110 반응식
C[O-].[Na+].[N:4]1([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][NH:22][C:23](=[O:29])[CH2:24][S:25][C:26](=O)[CH3:27])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.ClCC[CH2:33][OH:34].O>CO>[N:4]1([CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([O:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][NH:22][C:23](=[O:29])[CH2:24][S:25][CH2:26][CH2:27][CH2:33][OH:34])[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 962WaterHCID 123133-Chloro-1-propanolHCID 10942334Sodium MethoxideHCID 86750622N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(acetylthio)acetamide

생성물 1

HCID 67726286N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(3-hydroxypropylthio)acetamide수율 81%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

5 ml of a methanolic solution containing 0.26 g of a 28% w/v sodium methoxide solution were added, whilst ice-cooling, to a solution of 0.50 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(acetylthio)acetamide [prepared as described in step (b) above] in 5 ml of methanol, and the resulting solution was stirred for 20 minutes. At the end of this time, a solution of 0.11 ml of 3-chloro-1-propanol in 5 ml of methanol, was added, and the reaction mixture was heated under reflux for 5 hours. The solvent was then removed by distillation under reduced pressure. The residue thus obtained was mixed with water, and the aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the residue 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 0.42 g (yield 81%) of the title compound as an oil.

후처리

  1. additionwere added, whilst ice-
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 5 hours
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. extractionthe aqueous mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated by evaporation under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel
  9. additionby volume mixture of methanol and methylene chloride as the eluent

출처 및 근거

ORD 기록
ord-75936c190cbc4c32ab18f956ab1df720
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

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