Methanol → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]3-(mercapto)propionamide

HRID 52128Notes

Reaction equation

HRID 52128 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:27])[CH2:21][CH2:22][S:23]C(=O)C)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].CO>C(O)(=O)C>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:27])[CH2:21][CH2:22][SH:23])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 86750624N-[4-(4-Piperidinomethyl-2-pyridyloxy]-cis-2-butenyl]-3-(acetylthio)propionamide

Product 1

HCID 86750621N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]3-(mercapto)propionamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.0 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-3-(acetylthio)propionamide [prepared as described in step (a) above] and 0.49 g of a 28% w/v methanolic solution of sodium methoxide were added to 20 ml of methanol, whilst ice-cooling, and the mixture was stirred at the same temperature for 20 minutes. At the end of this time, 0.15 ml of acetic acid was added, and the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and condensed by evaporation under reduced pressure, to obtain 0.76 g (yield 85%) of the title compound as an oil.

Workup

  1. temperaturecooling
  2. customthe solvent was removed by distillation under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and condensed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ad9b2a64498143e2b1a7628e919d8cd4
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Reaction notes

Loading…