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

HRID 52108

Reaction equation

HRID 52108 reaction equation
C(N(CC)CC)C.[N:8]1([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([O:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][NH2:26])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>C(OCC)(=O)C>[N:8]1([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([O:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][NH:26][C:29](=[O:30])[CH2:28][Cl:27])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]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

0.54 ml of triethylamine was added to a solution of 1.00 g of 4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenylamine in 20 ml of ethyl acetate, and the resulting mixture was cooled. 0.31 ml of 2-chloroacetyl chloride were then added to the mixture. The reaction mixture was then stirred at room temperature for 1 hour, after which it 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 1:19 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.94 g (yield 73%) of the title compound as an oil.

Workup

  1. temperaturethe resulting mixture was cooled
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. concentrationThe extract was concentrated by evaporation under reduced pressure
  4. customthe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of methanol and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-51964fb84fdc4a97a1a24b02c9b357e6
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Linked notes

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