Acetone → HCID 19874499, compound

HRID 465457Notes

Reaction equation

HRID 465457 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](C2C=CC(CC3(OCCO3)C)=CC=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31](S(O)(=O)=O)=[CH:30][CH:29]=1.Cl.[CH3:40][C:41](C)=[O:42]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]=[CH:11][CH2:12][CH:13]1[C:31]1[CH:32]=[CH:33][C:28]([CH2:38][C:41](=[O:42])[CH3:40])=[CH:29][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 67895971HCID 67895971, compound

Product 1

HCID 19874499HCID 19874499, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture 1-benzyl-4-[4-(2,2-ethylene dioxypropyl)phenyl] piperidin-4-ol (3.0 g) and 4-toluenesulphonic acid (1.9 g) in benzene, was heated under reflux for 3 hr. using a Dean and Stark head. The cooled reaction mixture was washed with 1.2M sodium bicarbonate solution (1×50 ml) water, (2×50 ml , dried (magnesium sulphate), filtered, evaporated in vacuo, and chromatographed on silica. Elution with chloroform gave an oil which was dissolved in acetone and treated with 2M hydrochloric acid (5 ml) at room temperature for 4 h. The solvent was removed in vacuo, the residue dissolved in ether, washed with 1.2M sodium hydrogen carbonate (1×50 ml), water (2×50 ml), dried (magnesium sulphate), filtered and evaporated in vacuo to give 4-(1-benzyl-1,2,3,6-tetrahydropyridyl)phenyl propan-2-one, 1.5 g.

Workup

  1. temperatureunder reflux for 3 hr
  2. customThe cooled reaction mixture
  3. washwas washed with 1.2M sodium bicarbonate solution (1×50 ml) water
  4. dry with material(2×50 ml , dried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customchromatographed on silica
  8. washElution with chloroform
  9. customgave an oil which
  10. customThe solvent was removed in vacuo
  11. dissolutionthe residue dissolved in ether
  12. washwashed with 1.2M sodium hydrogen carbonate (1×50 ml), water (2×50 ml)
  13. dry with materialdried (magnesium sulphate)
  14. filtrationfiltered
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-f3d990d34d1e431d92d35ccce6d90b2c
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

Loading…