1,3-Dibromopropane → HCID 18599317, Verbindung

HRID 1906425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906425
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[NH2:15])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[C:9]2/[CH:10]([N:15]3[CH2:19][CH2:18][CH2:17]3)[CH2:11][CH2:12][CH2:13][CH2:14]/2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 53709014HCID 53709014, Verbindung2×

Produkt 1

HCID 18599317HCID 18599317, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customevaporated
  2. customThe aqueous layer was separated and saturated with solid potassium hydroxide
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customThe residue, 0.67 g, was chromatographed
  9. additioncontaining 0.5% ammonium hydroxide mixture as eluent
  10. washElution with 620 ml of this eluting mixture
  11. customgave mixtures of products
  12. washElution of the column contents with 5% methanol in chloroform containing 0.5% ammonium hydroxide (240 ml)
  13. customgave no product

Quellen und Nachweise

ORD-Eintrag
ord-ee0ee5a195d646f0b8410c61fb4ed755
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04652559

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