Water → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-chloroacetamide

HRID 52125

Reaction equation

HRID 52125 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][NH2:19])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>C(OCC)(=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:29](=[O:30])[CH2:28][Cl:27])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 136724732-Buten-1-amine, 4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-, (Z)-

Product 1

HCID 67725626N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-chloroacetamideYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.00 g of 4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenylamine was dissolved in 20 ml of ethyl acetate. 0.54 ml of triethylamine was added to the solution, and the resulting mixture was cooled in an ice bath. 0.31 ml of 2-chloroacetyl chloride was added, and the mixture was stirred for 1 hour at room temperature. At the end of this time, water was added, and the reaction mixture was extracted with ethyl acetate. The extract was condensed by evaporation under reduced pressure, and the residue was purified by silica gel chromatography, eluted with a 1:19 by volume mixture of methanol and ethyl acetate, to give 0.94 g (yield 73%) of the title compound as an oil.

Workup

  1. temperaturethe resulting mixture was cooled in an ice bath
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customcondensed
  4. customby evaporation under reduced pressure
  5. customthe residue was purified by silica gel chromatography
  6. washeluted with a 1:19 by volume mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-373d80380d2d45d0b2bb19c0f492ba9a
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Linked notes

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