Allyl bromide → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine

HRID 2166628Notes

Reaction equation

HRID 2166628 reaction equation
CC(C1C=CC(C2CNCCC=2)=C(O)C=1)(C)CCCCCC.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.[CH3:33][C:34]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH2:49][N:50]([CH2:54][CH:55]=[CH2:56])[CH2:51][CH2:52][CH:53]=2)=[C:44]([O:57]CC=C)[CH:43]=1)([CH3:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(O)C>[CH3:41][C:34]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH2:49][N:50]([CH2:54][CH:55]=[CH2:56])[CH2:51][CH2:52][CH:53]=2)=[C:44]([OH:57])[CH:43]=1)([CH3:33])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 155715613-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridineHCID 204997823-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine

Product 1

HCID 155715643-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridineYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.0 g. (3.32 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine, 539 mg. (3.90 mmoles) of anhydrous potassium carbonate and 401 mg. (3.32 mmoles) of allyl bromide in 23 ml. of ethanol is heated at reflux for 23 hours. The reaction mixture is concentrated under reduced pressure and the residue dissolved in 250 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed once with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 125 g. of silica gel eluted with 5% methanol-dichloromethane to yield 372 mg. (29%) of 3-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-1,2,5,6-tetrahydropyridine as an oil and 247 mg. (22%) of the title compound, M.P. 109°-110° C. (from ether-pentane).

Workup

  1. additionA mixture of 1.0 g
  2. temperatureat reflux for 23 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. dissolutionthe residue dissolved in 250 ml
  5. extractionThe organic extract
  6. washis washed once with 100 ml
  7. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  8. customevaporated to an oil
  9. customThe oil is purified via column chromatography on 125 g
  10. washof silica gel eluted with 5% methanol-dichloromethane
  11. customto yield 372 mg

Sources & evidence

ORD record
ord-e067eb6456c34e879aa0bb3a16a376fa
Source dataset
uspto-grants-1983_06
Patent number
US04387229

Reaction notes

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