1,2,3,6-Tetrahydropyridine → HCID 20548897, compound

HRID 1389845Notes

Reaction equation

HRID 1389845 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(=O)(O)[O-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14]>C1C=CC=CC=1>[Cl:18][C:17]([Cl:20])([Cl:19])[CH2:16][O:15][C:13]([N:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:14]

Participants

5

Reactant 3

HCID 127501,2,3,6-TetrahydropyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 20548897HCID 20548897, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

124.5 g (1.5 mol) of 1,2,5,6-tetrahydropyridine are dissolved in 1,200 ml of benzene. 124 g of sodium bicarbonate are introduced into this solution and the mixture is then cooled to 0° under a nitrogen atmosphere and, at this temperature, is treated slowly dropwise in the course of 31/2 hours with a solution of 316 g (1.5 mol) of 2,2,2-trichloroethyl chloroformate in 250 ml of benzene. The resulting white suspension is subsequently stirred for a further 15 hours at 0° and then poured into 2,000 ml of ice-water. The benzene phase is separated off and the aqueous phase is extracted by shaking with twice 1,000 ml of methylene chloride; the combined organic phases are washed with 1 N hydrochloric acid and then with a saturated solution of sodium chloride, dried over sodium sulphate and evaporated under a water pump vacuum, whereupon 1-(β,β,β-trichloroethoxycarbonyl)-1,2,5,6-tetrahydropyridine is obtained as a slightly reddish oil.

Workup

  1. temperaturethe mixture is then cooled to 0° under a nitrogen atmosphere and, at this temperature
  2. customThe benzene phase is separated off
  3. extractionthe aqueous phase is extracted
  4. stirringby shaking with twice 1,000 ml of methylene chloride
  5. washthe combined organic phases are washed with 1 N hydrochloric acid
  6. dry with materialwith a saturated solution of sodium chloride, dried over sodium sulphate
  7. customevaporated under a water pump vacuum

Sources & evidence

ORD record
ord-30e912b9db474414a4704f87641d3faf
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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