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

HRID 26077
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 26077
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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). Title Compound: PMR: αCDCl3TMS 0.85 (m, terminal methyl), 1.25 (s, gem dimethyl), 3.23 (m, allyl methylene), 5.0-5.4 and 5.5-6.1 (m, four vinyl protons), 6.82 (m, ArH) and 6.97 (d, J=8Hz, ArH).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-05de492b31c142d19b2ce60cff521002
Quelldatensatz
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04147872

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