HCID 68140142, compound → HCID 86733649, compound

HRID 1659200Notes

Reaction equation

HRID 1659200 reaction equation
[C:1]([NH:9][C@H:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][C@H:11]1[C:17]1[CH:22]=[CH:21][C:20]2[O:23][CH2:24][O:25][C:19]=2[CH:18]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[CH3:16][N:13]1[CH2:14][CH2:15][C@H:10]2[C@H:11]([C:17]3[CH:18]=[C:19]4[O:25][CH2:24][O:23][C:20]4=[CH:21][C:22]=3[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:9]2)[CH2:12]1

Participants

3

Reactant 1

HCID 68140142HCID 68140142, compound

Product 1

HCID 86733649HCID 86733649, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7.0 g of cis-4-benzoylamino-3-(3,4-methylenedioxyphenyl)-1-methylpiperidine are heated to 90° in 75 cc of phosphorus oxychloride for 20 hours. The reaction mixture is subsequently evaporated to dryness, the residue is dissolved in 50 cc of ice water and a saturated potassium carbonate solution is added until the mixture is strongly alkaline. The reaction mixture is extracted with chloroform, and the chloroform mixture is washed with water, dried over sodium sulphate, and the solvent is evaporated. The residue is taken up in 20 cc of ethanol, and absolute hydrochloric acid in ethanol is added until an acid reaction to Congo red is obtained and precipitation is effected with ether. The precipitate, the dihydrochloride of the title compound, is recrystallized from ethanol/ether. Yellow coloured crystals having a M.P. of 248° (decomp.).

Workup

  1. customThe reaction mixture is subsequently evaporated to dryness
  2. dissolutionthe residue is dissolved in 50 cc of ice water
  3. additiona saturated potassium carbonate solution is added until the mixture
  4. extractionThe reaction mixture is extracted with chloroform
  5. washthe chloroform mixture is washed with water
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is evaporated
  8. additionabsolute hydrochloric acid in ethanol is added until an acid reaction to Congo red
  9. customis obtained
  10. customprecipitation
  11. customThe precipitate, the dihydrochloride of the title compound, is recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-9ef8ecb7b60f42b3aceac950cd3c672e
Source dataset
uspto-grants-1976_06
Patent number
US03966938

Reaction notes

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