Chloroacetyl chloride → HCID 2063649, compound

HRID 348070Notes

Reaction equation

HRID 348070 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:21]([CH2:20][Cl:19])=[O:22])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471Triethylamine

Product 1

HCID 2063649HCID 2063649, compoundYield 383.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethoxycarbonylpiperazine (1.5 mL, 10 mmol) in 40 mL CH2Cl2, was added triethylamine (2 mL, 14 mmol) and chloroacetyl chloride (0.8 mL, 5.0 mmol) at 0° C. The resulting reaction mixture was stirred at amibent temperature for 2 hours. The reaction mixture was washed with water, 2N NaHSO4 and brine, and dried over sodium sulfate. The solvent was evaporated in vacuo to afford 1-ethoxycarbonyl-4-chloromethylcarbonylpiperazine (4.5 g) as an yellow oil, which was used without further purification.

Workup

  1. customThe resulting reaction mixture
  2. washThe reaction mixture was washed with water, 2N NaHSO4 and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fe7d47cc493040b6aea98c10405aaa21
Source dataset
uspto-grants-2007_02
Patent number
US07176207B2

Reaction notes

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