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

HRID 481347

Reaction equation

HRID 481347 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]1([CH3:18])[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Ca+2]>C(C(C)=O)C>[Cl:1][CH2:2][C:3]([N:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH3:18])[CH2:13][CH2:14]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10112Calcium CarbonateHCID 919652-Mepp

Product 1

HCID 47412122-Chloro-1-(4-o-tolylpiperazin-1-yl)ethanoneYield 83%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

Chloroacetyl chloride (4.5 ml, 56.6 mmol) is added dropwise to a solution of 1-o-tolylpiperazine (8.31 [lacuna], 47.2 mmol) and calcium carbonate (14.2 g, 142 mmol) in methyl ethyl ketone (100 ml) cooled to 0° C. The reaction mixture is stirred at this temperature for 1 h 30 and is then filtered through Celite. The Celite is rinsed several times with ethyl acetate and 3M sodium hydroxide solution. The two phases of the filtrate are then separated and the organic phase is dried over magnesium sulfate, filtered and concentrated to give the expected product in the form of a brown solid.

Workup

  1. filtrationis then filtered through Celite
  2. washThe Celite is rinsed several times with ethyl acetate and 3M sodium hydroxide solution
  3. customThe two phases of the filtrate are then separated
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f100b1ebd584b75824b3201336f9e84
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Linked notes

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