Water → 1-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(pyridin-3-yloxy)ethanone

HRID 516993Notes

Reaction equation

HRID 516993 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:11].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[S:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10](=[O:11])[CH2:9][O:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][CH2:16]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 679808471-(4-(Naphthalen-2-ylsulfonyl)piperazin-1-yl)-2-(pyridin-3-yloxy)ethanoneYield 11.46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-hydroxy pyridine (97 mg, 1.02 mmol), 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 5, 0.3 g, 0.85 mmol) and anhydrous potassium carbonate (0.352 g, 2.55 mmol) were stirred for over night in dry acetonitrile (20 mL). The mixture was poured into a large volume of water and the solution extracted with ether. Un-reacted phenol was removed with cold 1N NaOH solution. The ether extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by re-crystallization to yield the title compound (40 mg, 11.46% yield) as an off-white solid. 60% of the un-reacted starting material was also recovered from the reaction.

Workup

  1. extractionthe solution extracted with ether
  2. customUn-reacted phenol was removed with cold 1N NaOH solution
  3. extractionThe ether extract
  4. dry with materialwas dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by re-crystallization

Sources & evidence

ORD record
ord-29b531820d7e447888c66f2a435c32ad
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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