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

HRID 52056Notes

Reaction equation

HRID 52056 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a6cd11c93742421c8b780145cc125c38
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Reaction notes

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