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

HRID 26076Notes

Reaction equation

HRID 26076 reaction equation
CC(C1C=CC(C2CCCNC2)=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]([CH:48]2[CH2:53][CH2:52][CH2:51][N:50]([CH2:54][CH:55]=[CH2:56])[CH2:49]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]([CH:48]2[CH2:53][CH2:52][CH2:51][N:50]([CH2:54][CH:55]=[CH2:56])[CH2:49]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 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidineHCID 204997773-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-piperidine

Product 1

HCID 204997903-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propenyl)piperidineYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 900 mg. (2.97 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine, 481 mg. (3.48 mmoles) of anhydrous potassium carbonate and 359 mg. (2.97 mmoles) of allyl bromide in 20 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 under reduced pressure to an oil. The oil is purified via column chromatography on 125 g. of silica gel eluted with 25% cyclohexane-ether to yield 172 mg. (15%) of 3-[4-(1,1-dimethylheptyl)-2-allyloxyphenyl]-1-N-(2-propenyl)-piperidine as an oil and 411 mg. (40%) of the title compound as an oil. Title Compound: PMR: δCDCl3TMS 0.85 (m, terminal methyl), 1.25 (s, gem dimethyl), 3.1 (m, allyl methylene and C-2 or 6 methylene), 5.0-5.4 and 5.5-6.1 (m, three vinyl protons) and 6.8 (m, ArH).

Workup

  1. additionA mixture of 900 mg
  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 under reduced pressure to an oil
  9. customThe oil is purified via column chromatography on 125 g
  10. washof silica gel eluted with 25% cyclohexane-ether
  11. customto yield 172 mg

Sources & evidence

ORD record
ord-e78e92f50bfa441f9307e28b2e233ba3
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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