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

HRID 26076노트

반응식

HRID 26076 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e78e92f50bfa441f9307e28b2e233ba3
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147872

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