Potassium Carbonate → HCID 59837630, compound

HRID 273514Notes

Reaction equation

HRID 273514 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[Br:10][C:11]1[CH:12]=[C:13]([SH:17])[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:10][C:11]1[CH:12]=[C:13]([S:17][CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80597m-BromobenzenethiolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 59837630HCID 59837630, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-chloroethyl)pyrrolidine hydrochloride (1.0 equiv., 8.82 mmol) and 3-bromothiophenol (1.5 equiv., 13.23 mmol) were dissolved in acetonitrile (100 mL). Potassium carbonate (10.0 equiv., 88.2 mmol) was added to the reaction while stirring. The reaction was kept in oil bath at 80° C. to reflux for 18 h. The reaction was then cooled to room temperature and filtered to remove excess inorganics, and the organics were extracted with saturated NaHCO3 and brine. The organics were dried over Na2SO4 then concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography using 4:6 EtOAc/hexanes. The fractions were concentrated to afford product as a yellow oil (792.3 mg, 32% yield). Rf=0.75 MS (ES+): m/z=287 LC retention time: 1.81 min.

Workup

  1. customThe reaction was kept in oil bath at 80° C.
  2. temperatureto reflux for 18 h
  3. filtrationfiltered
  4. customto remove excess inorganics
  5. extractionthe organics were extracted with saturated NaHCO3 and brine
  6. dry with materialThe organics were dried over Na2SO4
  7. concentrationthen concentrated under reduced pressure
  8. customThe resulting crude oil was purified by flash chromatography
  9. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-86c6b6bc453247a48e428349a5f6746f
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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