Ethyl chloroacetate → HCID 53726615, compound

HRID 2413019Notes

Reaction equation

HRID 2413019 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:4].C(N(CC)CC)C.Cl[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C.C(Cl)(Cl)Cl>[F:15][C:2]([F:14])([F:1])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:12][CH2:13]1)=[O:4]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 204314422,2,2-Trifluoro-N-[2-(piperazin-1-yl)ethyl]acetamide

Product 1

HCID 53726615HCID 53726615, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1-(2-Trifluoroacetamidoethyl)piperazine (56 g, 0.25 mol), 37.5 ml of triethylamine, and 30.3 g (0.27 mol) of ethyl chloroacetate were combined in 200 ml of DMF. The temperature rose to 70° C. in 5 minutes. The reaction was allowed to stir overnight at room temperature, then filtered to remove triethylammonium hydrochloride. The solvent was removed, leaving an oily residue which was taken up in 250 ml of CHCl3 and washed with two 300 ml portions of H2O. The organic phase was separated, dried and evaporated to give 51 g of ethyl 4-(2-trifluoroacetamidoethyl)piperazine-1-acetate as a tan solid. This was not characterized. It was hydrolyzed by stirring for 6 hours in a solution of 20 g of KOH in 250 ml of 4:1 MeOH:H2O. The product was purified by chromatography on 1400 g of silica gel, eluting with 4:4:1 (v/v/v) CHCl3 :MeOH:conc. NH4OH. Recrystallization from MeOH gave 22.5 g of 4-(2-aminoethyl)piperazine-1-acetic acid as white crystals, m.p. 225° C. (dec).

Workup

  1. filtrationfiltered
  2. customto remove triethylammonium hydrochloride
  3. customThe solvent was removed
  4. customleaving an oily residue which
  5. washwashed with two 300 ml portions of H2O
  6. customThe organic phase was separated
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-6da5ae66b9fc4204b87dc329fd1b0952
Source dataset
uspto-grants-1985_01
Patent number
US04495281

Reaction notes

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