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

HRID 1266148Notes

Reaction equation

HRID 1266148 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 15 minutes 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 hours. The reaction mixture was washed with water (2×100 ml), dried (Na2SO4) and concentrated to give the title compound (D1) 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-89deeec60175475f955cb28c59aeb128
Source dataset
uspto-grants-2003_04
Patent number
US06548504B1

Reaction notes

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