1-Chloroethyl chloroformate → HCID 22678447, compound

HRID 1837685Notes

Reaction equation

HRID 1837685 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]3[O:22][CH2:23][O:24][C:17]=23)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[CH2:23]1[O:22][C:18]2[C:17](=[C:16]([CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[O:24]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22678633HCID 22678633, compound

Product 1

HCID 22678447HCID 22678447, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

20.3 g of 1-benzyl-4-(2,3-methylenedioxyphenethyl)piperidine was dissolved in 10 ml of 1,2-dichloroethane, 7 ml of 1-chloroethyl chloroformate was added thereto under ice-cooling, and the mixture was heated under reflux for 30 minutes. The solvent was evaporated, the resulting residue was dissolved in 100 ml of methanol, and the mixture was heated under reflux for one hour. The solvent was removed, the resulting residue was basified by adding a 5N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate), to give 13.1 g of the title compound as a pale yellow oil.

Workup

  1. temperatureunder ice-cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. customThe solvent was evaporated
  5. dissolutionthe resulting residue was dissolved in 100 ml of methanol
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for one hour
  8. customThe solvent was removed
  9. additionby adding a 5N aqueous sodium hydroxide
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe crude product was purified by NH
  15. customform silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-88f0c6ee46cd4ecda9f84b26083fd5cb
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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