Water → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-chloroacetamide

HRID 52094Notes

Reaction equation

HRID 52094 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][CH2:23][CH2:24][NH2:25])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl:26][CH2:27][C:28](Cl)=[O:29].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][CH2:23][CH2:24][NH:25][C:28](=[O:29])[CH2:27][Cl:26])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine

Product 1

HCID 19962925N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-2-chloroacetamideYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.68 ml of triethylamine were added to a solution of 3.00 g of 3-(4-piperidinomethyl-2-pyridyloxy)propylamine in 60 ml of ethyl acetate, and the resulting mixture was cooled with ice, after which 0.96 ml of 2-chloroacetyl chloride was added. 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 concentrate was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and ethyl acetate as the eluent, to give 3.40 g (yield 87%) of the title compound as an oil.

Workup

  1. temperaturethe resulting mixture was cooled with ice
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. concentrationThe extract was concentrated by evaporation under reduced pressure
  4. customthe concentrate 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-cbb3be641e5546b88ff33cc13ba4f545
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Reaction notes

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