Sodium Carbonate → HCID 68464755, compound

HRID 505866Notes

Reaction equation

HRID 505866 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][O:12][C:11]2=[O:16])[CH2:4][CH2:3]1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:21]=[CH:20][C:19]([CH2:18][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][N:10]3[C:14](=[O:15])[CH2:13][O:12][C:11]3=[O:16])[CH2:4][CH2:3]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 154634-Phenylbenzyl chlorideHCID 68465725HCID 68465725, compound

Product 1

HCID 68464755HCID 68464755, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.40 g (1.61 mmol) of 3-(2-piperidin-4-ylethyl)-1,3-oxazolidine-2,4-dione hydrochloride, prepared in step 1.1., 0.326 g (1.61 mmol) of 4-(chloromethyl)biphenyl and 0.51 g (4.82 mmol) of sodium carbonate in 3 ml of acetonitrile is heated at reflux for 17 hours. It is left to return to ambient temperature and filtered and the filtrate is concentrated under reduced pressure. The residue is taken up in dichloromethane and water and the aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Following evaporation of the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 97/3 then 95/5 mixture of dichloromethane and methanol.

Workup

  1. temperatureat reflux for 17 hours
  2. waitIt is left
  3. customto return to ambient temperature
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customwater and the aqueous phase is separated off
  7. extractionextracted twice with dichloromethane
  8. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. customevaporation of the solvent
  11. customthe residue obtained
  12. customis purified by chromatography on silica gel
  13. washeluting with a 97/3
  14. addition95/5 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-48f0cb2b5a3941609f9c1b0179b2573f
Source dataset
uspto-grants-2010_08
Patent number
US07781590B2

Reaction notes

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