Methylamine → 2-(Methylamino)-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone

HRID 516995Notes

Reaction equation

HRID 516995 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].C1COCC1.[CH3:29][NH2:30]>O>[CH3:29][NH:30][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 679809942-(Methylamino)-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanoneYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 5, 0.1 g, 0.85 mmol) in THF (10 mL) diisopropyl ethyl amine (81 mg, 0.62 mmol) was added at 0° C. followed by methyl amine solution (30% solution, 10 mL). The reaction mixture was allowed to stir for overnight at room temperature. The reaction mixture was poured into a large volume of water (50 mL) and the solution was extracted with ethyl acetate. The combined organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to obtain the title compound (20.0 mg, 22.90% yield) as an off-white solid.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-3633194601344ba398ef464875931c0e
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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