Chloroacetyl chloride → 2-Chloro-1-(4-ethylpiperazin-1-yl)ethanone

HRID 1455520Notes

Reaction equation

HRID 1455520 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[CH2:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:14]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:18]1[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 791961-Ethylpiperazine

Product 1

HCID 43847022-Chloro-1-(4-ethylpiperazin-1-yl)ethanoneYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (6.63 ml) and triethylamine (13.4 ml) in DCM (20 ml) was added dropwise to 1-ethylpiperazine (10 g) in DCM (60 ml) under nitrogen. The mixture was stirred at room temperature for 17 hours then partitioned between DCM and H2O (100 ml). The aqueous layer was neutralised using 1M NaOH before extracting into DCM. Organic layer dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (silica, 0 to 5% MeOH in DCM) gave the title compound as a pale oil (3.23 g, 19%). δH (CDCl3) 4.08 (2H, s), 3.65 (2H, m), 3.55 (2H, m), 2.52-2.40 (6H, m), 1.10 (3H, t, J 7.2 Hz).

Workup

  1. customthen partitioned between DCM and H2O (100 ml)
  2. extractionbefore extracting into DCM
  3. dry with materialOrganic layer dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (silica, 0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-8228b3e6490342529250cbcb99f81808
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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