Hydrochloric Acid → HCID 86736579, compound

HRID 1389846Notes

Reaction equation

HRID 1389846 reaction equation
[O:1]1[CH:7]2[CH:2]1[CH2:3][N:4]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[CH2:5][CH2:6]2.[ClH:16]>O1CCOCC1.O>[OH:1][C@H:2]1[C@H:7]([Cl:16])[CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20548869HCID 20548869, compound

Product 1

HCID 86736579HCID 86736579, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5.0 g (0.018 mol) of 3,4-epoxy-1-(β,β,β-trichloroethoxycarbonyl)-piperidine are dissolved in 50 ml of dioxane and the solution is treated with 60 ml of 6 N hydrochloric acid. The slightly exothermic reaction is kept at room temperature by means of a water bath, and the reaction mixture is stirred for 15 hours, then diluted with water and extracted with 3 times 100 ml of methylene chloride. The organic phase is washed with 0.1 N sodium hydroxide solution and then with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and then evaporated to dryness, first under a water pump vacuum and then under a high vacuum, whereupon trans-3-hydroxy-4-chloro-1-(β,β,β-trichloroethoxycarbonyl)-piperidine is obtained in the form of a slightly yellow oil.

Workup

  1. customThe slightly exothermic reaction
  2. customis kept at room temperature by means of a water bath
  3. extractionextracted with 3 times 100 ml of methylene chloride
  4. washThe organic phase is washed with 0.1 N sodium hydroxide solution
  5. dry with materialwith a saturated aqueous solution of sodium chloride, dried over sodium sulphate
  6. customevaporated to dryness, first under a water pump vacuum

Sources & evidence

ORD record
ord-a15dbaff64cd45f6a805762bc08af955
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

Loading…