Triethylamine → [4-(2,5-Dimethyl-phenyl)-piperazin-1-yl]-[1-(4-fluoro-2-methyl-phenyl)-4-(3-methoxy-benzenesulfonyl)-piperazin-2-yl]-methanone

HRID 2065751Notes

Reaction equation

HRID 2065751 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([CH:18]2[CH2:23][NH:22][CH2:21][CH2:20][N:19]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])=[O:17])[CH2:12][CH2:11]1.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([S:40](Cl)(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([CH:18]2[CH2:23][N:22]([S:40]([C:36]3[CH:37]=[CH:38][CH:39]=[C:34]([O:33][CH3:32])[CH:35]=3)(=[O:42])=[O:41])[CH2:21][CH2:20][N:19]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])=[O:17])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 44474092HCID 44474092, compound

Product 1

HCID 25188663[4-(2,5-Dimethyl-phenyl)-piperazin-1-yl]-[1-(4-fluoro-2-methyl-phenyl)-4-(3-methoxy-benzenesulfonyl)-piperazin-2-yl]-methanoneYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-[1-(4-fluoro-2-methyl-phenyl)-piperazin-2-yl]-methanone hydrochloride (42 mg) in DMF (1 mL) was added 3-methoxybenzene sulfonyl chloride (21.4 mg) and triethyl amine (40 μL). The reaction mixture was stirred at ambient temperature for 2 h, was diluted with ethyl acetate and washed with a saturated aqueous solution of NaHCO3. The combined organic phases were washed with water and brine, dried (Na2SO4), filtered and evaporated. The crude product was purified by column chromatography (SiO2, n-heptane/ethyl acetate 2:1) to give [4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-[1-(4-fluoro-2-methyl-phenyl)-4-(3-methoxy-benzenesulfonyl)-piperazin-2-yl]-methanone (42 mg) as white solid, MS: 581.3 ([M+H]+).

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by column chromatography (SiO2, n-heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-0163105cd8f5411884b87e8e84bd7fa0
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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