Chloroform → (4-Bromo-2-methylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804014Notes

Reaction equation

HRID 1804014 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([CH3:25])[CH:17]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C(Cl)(Cl)Cl>CO>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:12]2[CH2:11][CH2:10][N:9]([C:3]3[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=3)[CH2:14][CH2:13]2)=[O:21])=[C:18]([CH3:25])[CH:17]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 995704-Bromo-2-methylbenzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazine

Product 1

HCID 58484835(4-Bromo-2-methylphenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-(3,5-dimethylpyridin-2-yl)piperazine (3.8 g) described in Preparation Example 47, 4-bromo-2-methylbenzoic acid (4.3 g) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (8.8 g) were added chloroform (30 mL) and methanol (30 mL), and the mixture was stirred at room temperature overnight. After evaporation of the solvent, ethyl acetate was added, and insoluble materials were filtered off. The solvent in the filtrate was evaporated, and the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (7 g).

Workup

  1. customAfter evaporation of the solvent, ethyl acetate
  2. additionwas added
  3. filtrationinsoluble materials were filtered off
  4. customThe solvent in the filtrate was evaporated
  5. customthe residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6d18ea0f565248b2ac382bfe94166ec9
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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