Water → 2-(2-Piperazin-1-ylethoxy)acetamide

HRID 1383751Notes

Reaction equation

HRID 1383751 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][C:6]([NH2:8])=[O:7].[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.O>C1(C)C=CC=CC=1>[N:9]1([CH2:2][CH2:3][O:4][CH2:5][C:6]([NH2:8])=[O:7])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 110189312-(2-Chloroethoxy)acetamide

Product 1

HCID 211883622-(2-Piperazin-1-ylethoxy)acetamideYield 39.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 13.15 g of (2-chloroethoxy)acetamide (0.1 mol) and 43 g of anhydrous piperazine (0.5 mol) in 250 ml of toluene is introduced into a round-bottomed flask fitted with a water-cooled condenser and a mechanical stirrer. The mixture is heated at the reflux temperature for 4 hours. The precipitate formed is filtered off while hot and the solvent of the filtrate is evaporated off under reduced pressure to dryness. The evaporation residue is purified by chromatography on silica gel (eluent: 14/5/1 (v/v/v) of dichloromethane/methanol/28% aqueous ammonia solution). 7.4 g of 2-[2-(1-piperazinyl)ethoxy]acetamide are obtained in the form of a yellow oil. Yield: 39% Mass spectrum: 188 (MH+), 99 (HN(C4H8)N+=CH2), 44 (CONH2).

Workup

  1. additionis introduced into a round-bottomed flask
  2. temperaturecooled condenser and a mechanical stirrer
  3. temperatureThe mixture is heated at the reflux temperature for 4 hours
  4. customThe precipitate formed
  5. filtrationis filtered off while hot and the solvent of the filtrate
  6. customis evaporated off under reduced pressure to dryness
  7. customThe evaporation residue is purified by chromatography on silica gel (eluent: 14/5/1 (v/v/v) of dichloromethane/methanol/28% aqueous ammonia solution)

Sources & evidence

ORD record
ord-02214f4e121e4dc189ef496d532ac9ab
Source dataset
uspto-grants-2001_07
Patent number
US06255487B1

Reaction notes

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