Ammonia → HCID 21523329, compound

HRID 918162Notes

Reaction equation

HRID 918162 reaction equation
[C:1]1([CH2:7][CH:8]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]([CH3:17])=[C:10]([CH3:16])[CH2:11][CH2:12]OCC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>Br>[CH2:19]([N:18]1[CH2:12][CH2:11][C:10]([CH3:16])=[C:9]([CH3:17])[CH:8]1[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54525597HCID 54525597, compound

Product 1

HCID 21523329HCID 21523329, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

10 ml of 48% hydrobromic acid is added to 1 g of 1-phenyl-2-(N-benzyl)amino-3,4-dimethyl-6-ethoxy-3-hexene obtained according to the procedure described in Example 13 and the mixture is refluxed for 5 minutes. After cooling, the mixture is neutralized with an aqueous ammonia and extracted with ethyl ether. The ether layer is washed with water and dried with sodium sulfate. The solvent is removed by distillation. The residue is dissolved in 10 ml of acetone. 1 g of sodium hydrogen carbonate is added to the solution and refluxed for 5 hours. Insoluble matters are removed by filtration. The solvent is distilled off. The residue is purified by a silica gel chromatography using chloroform, methanol and acetic acid (90:10:5). As the result, 0.2 g of 1,2-dibenzyl-3,4-dimethyl-1,2,5,6-tetrahydropyridine is obtained. The free amine is dissolved in acetone and oxalic acid is added to the solution to obtain the oxalate of 1,2-dibenzyl-3,4-dimethyl-1,2,5,6-tetrahydropyridine.

Workup

  1. customobtained
  2. temperaturethe mixture is refluxed for 5 minutes
  3. temperatureAfter cooling
  4. extractionextracted with ethyl ether
  5. washThe ether layer is washed with water
  6. dry with materialdried with sodium sulfate
  7. customThe solvent is removed by distillation
  8. dissolutionThe residue is dissolved in 10 ml of acetone
  9. addition1 g of sodium hydrogen carbonate is added to the solution
  10. temperaturerefluxed for 5 hours
  11. customInsoluble matters are removed by filtration
  12. distillationThe solvent is distilled off
  13. customThe residue is purified by a silica gel chromatography

Sources & evidence

ORD record
ord-d3092dfca4ab41fd8089a7a576e963ed
Source dataset
uspto-grants-1976_07
Patent number
US03969468

Reaction notes

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