1-(2-Methoxyphenyl)piperazine → 2-(4-Trichloroacetylpiperazin-1-yl) anisole

HRID 429136Notes

Reaction equation

HRID 429136 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:15][C:16]([Cl:21])([Cl:20])[C:17]([N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)=[O:18]

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6420Trichloroacetyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 33831142-(4-Trichloroacetylpiperazin-1-yl) anisoleYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2-methoxyphenyl) piperazine (7.0 g) in dichloromethane (30 ml) was added over 0.25 h to a stirred solution of trichloroacetyl chloride (4.06 ml) in dichloromethane (40 ml) at room temperature under argon. Diisopropylethylamine (5.95 ml) was then added and the whole was stirred for 18 h. The reaction mixture was washed with water (2×100 ml), dried (Na2SO4) and concentrated to give the title compound (D3) as an oil (11.2 g, 91%). MH+337/339.

Workup

  1. washThe reaction mixture was washed with water (2×100 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ffc611fd850b4532b41cec8f3e56df6e
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Reaction notes

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