4-Methylmorpholine → HCID 67381202, compound

HRID 1804410Notes

Reaction equation

HRID 1804410 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][C:11]1=[O:16].[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:19]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>CO.C(Cl)(Cl)Cl>[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:13]2[CH2:14][CH2:15][N:10]([C:4]3[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=3[CH3:2])[C:11](=[O:16])[CH2:12]2)=[O:23])=[C:20]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:19]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27610574-Bromo-2-methanesulfonylbenzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 67381048HCID 67381048, compound

Product 1

HCID 67381202HCID 67381202, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 1-(2,4-dimethylphenyl)piperazin-2-one hydrochloride (1.2 g), 4-bromo-2-methanesulfonylbenzoic acid (1.4 g) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (2.1 g) were added chloroform (7.5 mL), methanol (7.5 mL) and N-methylmorpholine (550 μL), and the mixture was stirred at room temperature overnight. After evaporation of the solvent, the residue was purified by column chromatography (chloroform) to give 4-(4-bromo-2-methanesulfonylbenzoyl)-1-(2,4-dimethylphenyl)piperazin-2-one (2.24 g).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record
ord-5b3472cea0f04da7845071c8aa6bdb47
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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