Aniline → 1-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(phenylamino)ethanone

HRID 516994Notes

Reaction equation

HRID 516994 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[CH2:23][CH2:22]1)=[O:20]>C(#N)C>[CH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[S:27]([N:24]1[CH2:23][CH2:22][N:21]([C:19](=[O:20])[CH2:18][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:25]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 679804171-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(phenylamino)ethanoneYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of aniline (15.3 g, 0.16 mol) and di-isopropyl ethylamine (DIEA, 56 mL, 0.33 mol) in acetonitrile (120 mL) is heated to 60° C. and 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 5, 0.3 g, 0.85 mmol) is added dropwise. The reaction mixture is kept stirring at this temperature for another 3 h and is then evaporated to dryness. Water is added to the residue, and extracted with ethyl acetate (2×30 mL). The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The resultant crude product was purified by column chromatography on silica gel (hexane:ethyl acetate:3:7) to obtain the title compound (300 mg, 76.53%) as an off-white solid.

Workup

  1. customis then evaporated to dryness
  2. additionWater is added to the residue
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant crude product was purified by column chromatography on silica gel (hexane:ethyl acetate:3:7)

Sources & evidence

ORD record
ord-026d16cb4369425b8cedeed47607e5c2
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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