Triethylamine → [4-(2-Chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxyphenyl)methanone

HRID 1954022Notes

Reaction equation

HRID 1954022 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[Cl:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>ClCCl>[Cl:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[N:24]1[CH2:29][CH2:28][N:27]([C:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=2)=[O:7])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 151240931-(2-Chloro-3-methylphenyl)piperazine

Product 1

HCID 15434661[4-(2-Chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxyphenyl)methanoneYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4,5-Trimethoxybenzoyl chloride (2.03 g, 8.8 mmol) in dichloromethane (10 mL) is added dropwise to a solution of 2-chloro-3-methylphenyl piperazine (1.98 g, 8.0 mmol) and triethylamine (4.5 mL, 32.0 mmol) in dichloromethane (90 mL) and stirred for 2 hours at room temperature. The reaction mixture is washed with water, dried (magnesium sulfate), and concentrated in vacuo. The resulting solid is purified by medium pressure liquid chromatography (MPLC) on silica gel eluting with 40% ethyl acetate/hexane to give 2.52 g of the title compound as a white solid; mp 156-159° C.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid is purified by medium pressure liquid chromatography (MPLC) on silica gel eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1f08dda140ae4ce5b7df6f24ae85275e
Source dataset
uspto-grants-2000_09
Patent number
US06121267

Reaction notes

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