Benzyl Alcohol → 2-(Benzyloxy)-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone

HRID 516991Notes

Reaction equation

HRID 516991 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)(=[O:23])=[O:22])[CH2:17][CH2:16]1)=[O:14]>C1COCC1>[CH2:3]([O:10][CH2:12][C:13]([N:15]1[CH2:16][CH2:17][N:18]([S:21]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)(=[O:22])=[O:23])[CH2:19][CH2:20]1)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×

Product 1

HCID 679805472-(Benzyloxy)-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanoneYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (35.88 mg, 60 percent in oil) in dry THF (20 mL) cooled to 0° C. under nitrogen atmosphere, a solution of benzylalcohol (0.09 g, 0.717 mmol) in THF (1 mL) was added drop wise to the mixture over 25 minutes, and the mixture was brought to room temperature and stirred for 2 h. The reaction was again cooled to 0° C., to which a solution of 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 5) in THF (20 mL) was added drop wise over 30 minutes. After being stirred for over night at room temperature, the reaction mixture was poured into ice cold water and extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant crude product was purified by column chromatography on silica gel (hexane:ethyl acetate:1:1) to obtain the title product (60 mg, 24%) as an off-white solid.

Workup

  1. customwas brought to room temperature
  2. additionwas added drop wise over 30 minutes
  3. stirringAfter being stirred for over night at room temperature
  4. additionthe reaction mixture was poured into ice cold water
  5. extractionextracted with ethyl acetate (2×10 mL)
  6. washThe organic layer was washed with brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant crude product was purified by column chromatography on silica gel (hexane:ethyl acetate:1:1)

Sources & evidence

ORD record
ord-146103ca6b3f4ad7833e06879010c02e
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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