Potassium Carbonate → HCID 68023394, compound

HRID 517006Notes

Reaction equation

HRID 517006 reaction equation
[CH3:1][C@@H:2]1[NH:7][C@H:6]([CH3:8])[CH2:5][N:4]([S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[O:28]([CH2:35][C:36](Cl)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[CH3:8][C@H:6]1[CH2:5][N:4]([S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])[CH2:3][C@@H:2]([CH3:1])[N:7]1[C:36](=[O:37])[CH2:35][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69703Phenoxyacetyl chlorideHCID 66847758rel-(3R,5S)-3,5-Dimethyl-1-(2-naphthalenylsulfonyl)piperazine

Product 1

HCID 68023394HCID 68023394, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

In a two neck round bottom flask (3S,5R)-3,5-dimethyl-1-(naphthalen-2-yl-sulfonyl)piperazine (100 mg, 0.33 moles) was dissolved in 25 mL of acetonitrile. K2CO3 (71 mg, 0.53 moles) was added to the reaction flask at room temperature under nitrogen atmosphere and allowed the reaction mixture to stir for about 10 min. The flask was then cooled to 0° C. and phenoxy acetyl chloride (83 μl, 0.49 moles) was added to the reaction flask drop wise at the same temperature. After addition, the reaction mixture was slowly warmed to room temperature and allowed it to stir for 3 hr. TLC indicated complete consumption of the starting material. The reaction was quenched with cold water (25 mL) and extracted with ethyl acetate (2×25 mL). The combined organic phase was washed with brine solution and dried over sodium sulphate. Solvent was removed under reduced pressure to give crude material which was purified by column chromatography (20% ethyl acetate and hexane) to afford the title compound with 98% purity.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was slowly warmed to room temperature
  3. stirringto stir for 3 hr
  4. customconsumption of the starting material
  5. customThe reaction was quenched with cold water (25 mL)
  6. extractionextracted with ethyl acetate (2×25 mL)
  7. washThe combined organic phase was washed with brine solution
  8. dry with materialdried over sodium sulphate
  9. customSolvent was removed under reduced pressure
  10. customto give crude material which
  11. customwas purified by column chromatography (20% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-d215e618b4f54e5dba68838368d8182e
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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