Allyl bromide → HCID 13023230, compound

HRID 1156986Notes

Reaction equation

HRID 1156986 reaction equation
C1(C23CCCC2CNCC3)C=CC=CC=1.C(=O)(O)[O-].[Na+].C(Br)C=C.[Br-].[C:26]1([C:32]23[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:36][NH+:35]([CH2:41][CH:42]=[CH2:43])[CH2:34][CH2:33]3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[C:26]1([C:32]23[CH2:40][CH2:39][CH2:38][CH:37]2[CH2:36][N:35]([CH2:41][CH:42]=[CH2:43])[CH2:34][CH2:33]3)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 20534426HCID 20534426, compoundHCID 70546502HCID 70546502, compound

Product 1

HCID 13023230HCID 13023230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g. of 4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine in 30 ml. of N,N-dimethylformamide containing 1.23 g. of sodium bicarbonate was stirred at 25° C. while 1.23 g. of 2-propenyl bromide was added in one portion. The reaction mixture was stirred and heated at reflux for four hours. After being cooled to room temperature, the reaction mixture was filtered and concentrated to an oil under reduced pressure. The residual oil was dissolved in 300 ml. of diethyl ether. The ethereal solution was washed with water, dried, and the solvent was then removed by evaporation under reduced pressure, thus providing 4a-phenyl-2-(2-propenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine as an oil. The oil so formed was dissolved in 150 ml. of fresh diethyl ether, and hydrogen bromide gas was bubbled through the ethereal solution. The precipitated salt was collected by filtration and recrystallized from diisopropyl ether and isopropanol to afford 1.3 g. of 4a-phenyl-2-(2-propenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H- 2-pyrindinium bromide. M.P. 185°-187° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for four hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated to an oil under reduced pressure
  5. dissolutionThe residual oil was dissolved in 300 ml
  6. washThe ethereal solution was washed with water
  7. customdried
  8. customthe solvent was then removed by evaporation under reduced pressure, thus providing 4a-phenyl-2-(2-propenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine as an oil
  9. customThe oil so formed
  10. dissolutionwas dissolved in 150 ml
  11. customof fresh diethyl ether, and hydrogen bromide gas was bubbled through the ethereal solution
  12. filtrationThe precipitated salt was collected by filtration
  13. customrecrystallized from diisopropyl ether and isopropanol
  14. customto afford 1.3 g

Sources & evidence

ORD record
ord-f6e23955d5064f1e8f7222bc57a629eb
Source dataset
uspto-grants-1982_06
Patent number
US04337341

Reaction notes

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