HCID 86736580, compound → HCID 13192236, compound

HRID 1389848Notes

Reaction equation

HRID 1389848 reaction equation
[OH:1][C@H:2]1[C@H:7]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][N:4](C(OCC(Cl)(Cl)Cl)=O)[CH2:3]1>C(O)(=O)C.[Zn]>[OH:1][C@H:2]1[C@H:7]([S:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 86736580HCID 86736580, compound

Product 1

HCID 13192236HCID 13192236, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

14.0 g (0.036 mol) of trans-3-hydroxy-4-phenylthio-1-(β,β,β-trichloroethoxycarbonyl)-piperidine are dissolved in 140 ml of 90% acetic acid and the solution is treated with 9.5 g (0.14 mol) of zinc dust in portions. The reaction mixture is subsequently stirred for one hour at room temperature and then filtered through a layer of diatomaceous earth. The filtrate is evaporated under a high vacuum, the resulting residue is taken up in 500 ml of water, the solution is cooled to 0° in an ice-water bath and, at this temperature, rendered strongly alkaline with concentrated sodium hydroxide solution and the reaction mixture is extracted by shaking with 3 times 200 ml of methylene chloride. The combined organic phases are washed once with water, dried over sodium sulphate and evaporated under a water pump vacuum, whereupon trans-3-hydroxy-4-phenylthio-piperidine is obtained in the form of the crystalline crude base, which is recrystallised from methanol/ether; melting point 135°-136°. The neutral fumarate prepared from the base with fumaric acid crystallises from methanol/ether; melting point 171°-173°.

Workup

  1. filtrationfiltered through a layer of diatomaceous earth
  2. customThe filtrate is evaporated under a high vacuum
  3. temperaturethe solution is cooled to 0° in an ice-water bath and, at this temperature
  4. extractionthe reaction mixture is extracted
  5. stirringby shaking with 3 times 200 ml of methylene chloride
  6. washThe combined organic phases are washed once with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated under a water pump vacuum

Sources & evidence

ORD record
ord-a00d7aa890ee4557b86e32de9e0e50a3
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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