Reaktion #1993607

Reaktionsgleichung

N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine

1,3-dibromopropane

potassium carbonate

N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine

→

(±)-(E)-1-[2-[(4-methylphenyl)methylene]cyclohexyl]-azetidine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated
2. 2
   SonstigeThe aqueous layer was separated and saturated with solid potassium hydroxide
3. 3
   Extraktionextracted with diethyl ether
4. 4
   ExtraktionThe ether extract
5. 5
   Waschenwas washed with saturated sodium chloride solution
6. 6
   Trocknendried with magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue, 0.67 g, was chromatographed
9. 9
   workup.ADDITIONcontaining 0.5% ammonium hydroxide mixture as eluent
10. 10
    WaschenElution with 620 ml of this eluting mixture
11. 11
    Sonstigegave mixtures of products
12. 12
    WaschenElution of the column contents with 5% methanol in chloroform containing 0.5% ammonium hydroxide (240 ml)
13. 13
    Sonstigegave no product

Vorschrift

A mixture of N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine, from step C above, 0.64 g (3.2 mmol) with 1.28 g (6.4 mmol) of 1,3-dibromopropane and 0.88 g (6.4 mmol) of potassium carbonate in 20 ml of ethanol was refluxed 18 hr, evaporated and the residue was taken up in a water/diethyl ether mixture. The aqueous layer was separated and saturated with solid potassium hydroxide and extracted with diethyl ether. The ether extract was washed with saturated sodium chloride solution, dried with magnesium sulfate and evaporated. The residue, 0.67 g, was chromatographed using a HPLC Merck C silica gel column using a 3% methanol in chloroform solution containing 0.5% ammonium hydroxide mixture as eluent. Elution with 620 ml of this eluting mixture gave mixtures of products containing the N-allyl derivative of the starting N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine. Elution of the column contents with 5% methanol in chloroform containing 0.5% ammonium hydroxide (240 ml) gave no product. The next 540 ml gave 180 mg of (±)-(E)-1-[2-[(4-methylphenyl)methylene]cyclohexyl]-azetidine. GC analyses (3% SE 30) 100% at 4.99 min, UV λmax(ε)247(15,300). HR mass spectrum Found 241.1844, Calcd. for C17H23N 241.1830. The NMR spectrum was also consistent for this named product.

Quelle