HCID 53994200, compound → HCID 21426500, compound

HRID 2398291Notes

Reaction equation

HRID 2398291 reaction equation
C(O[C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH:7]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C>O>[CH3:12][N:9]1[CH2:10][CH2:11][CH:6]2[CH2:5][C:4](=[O:20])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13][CH:7]2[CH2:8]1

Participants

3

Reactant 1

HCID 53994200HCID 53994200, compound

Product 1

HCID 21426500HCID 21426500, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

27 g of 3-benzyl-1-methyl-4-piperidine-acetic acid ethyl ester are slowly added to 250 g of polyphosphoric acid previously heated to 100°, the temperature is raised to 130° and the reaction mixture is stirred at this temperature for 2 hours. After cooling to room temperature the reaction mixture is poured on 1 liter of water, the resulting solution is washed out with ether and made alkaline with potassium carbonate (pH 9 to 10). The 1,2,3,4,4a5,11,11a-octahydro-2-methyl-6H-benzo[5,6]-cyclohepta[1,2-c]pyridin-6-one which separates as an oil, is extracted with ether, the extracts are washed with water, dried over sodium sulphate, concentrated by evaporation and distilled in a high vacuum. The mixture of isomers has a B.P. of 135°-140° 10.05 mm Hg.

Workup

  1. temperaturepreviously heated to 100°
  2. temperaturethe temperature is raised to 130°
  3. washthe resulting solution is washed out with ether
  4. extractionis extracted with ether
  5. washthe extracts are washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. distillationdistilled in a high vacuum
  9. additionThe mixture of isomers

Sources & evidence

ORD record
ord-a796a7a764584c359c2b995d2de0807a
Source dataset
uspto-grants-1977_05
Patent number
US04024265

Reaction notes

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