HCID 20463187, compound → HCID 18423351, compound

HRID 325958Notes

Reaction equation

HRID 325958 reaction equation
ClC(Cl)(Cl)COC([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:9][CH2:8]1)=O>C(O)(=O)C.O1CCCC1.O.[Zn]>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[O:13][CH:10]1[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]1

Participants

6

Reactant 1

HCID 20463187HCID 20463187, compound

Product 1

HCID 18423351HCID 18423351, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resulting 1-(2,2,2-trichloroethoxycarbonyl)-4-(2-naphthalenyloxy)piperidine is dissolved in a mixture of 250 ml of acetic acid, 250 ml of tetrahydrofuran and 125 ml of water. 28.5 g (0.436 mole) of zinc dust is added in portions with stirring and the exothermic reaction allowed to proceed for 21/2 hours. The mixture is filtered and the solvents are removed in vacuo. The residue is partitioned between ether and aqueous sodium hydroxide and the organic phase washed with water and extracted with dilute aqueous hydrochloric acid. The acid extracts are washed with ether, made basic with sodium hydroxide and extracted into ether and toluene and the organic solution washed, dried over magnesium sulfate and concentrated in vacuo to yield 4-(2-naphthalenyloxy)piperidine, which is redissolved in ethanol/ether and treated with dry HCl, and the hydrochloride salt recrystallized from butanone/methanol. M.P. 229.5°-231.5° C.

Workup

  1. customthe exothermic reaction
  2. custom2 hours
  3. filtrationThe mixture is filtered
  4. customthe solvents are removed in vacuo
  5. customThe residue is partitioned between ether and aqueous sodium hydroxide
  6. washthe organic phase washed with water
  7. extractionextracted with dilute aqueous hydrochloric acid
  8. washThe acid extracts are washed with ether
  9. extractionextracted into ether and toluene
  10. washthe organic solution washed
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e45844f69e5f419baee74e955633d59e
Source dataset
uspto-grants-1984_04
Patent number
US04443462

Reaction notes

Loading…