1,3-Propanediamine → 1-[1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,5-diazapentane

HRID 1390553

Reaktionsgleichung

Reaktionsgleichung von HRID 1390553
[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH:14]1[C:19]([CH3:21])([CH3:20])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2.[NH2:25][CH2:26][CH2:27][CH2:28][NH2:29].C1(C)C=CC=CC=1>O>[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][CH:11]([NH:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:12][CH2:13][CH:14]1[C:19]([CH3:21])([CH3:20])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2

Komponenten

5

Edukt 3

HCID 4281,3-PropanediamineHCID 1140TolueneHCID 213328461,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanone

Produkt 1

HCID 213328411-[1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,5-diazapentane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanone (6.04 g., 0.02 mole) and 1,3-diaminopropane (0.10 mole) in 150 ml. toluene is heated at reflux overnight with a Dean-Stark water separator. The cooled solution is concentrated under reduced pressure. The residue is dissolved in ethanol and hydrogenated with PtO2 at room temperature and 40 psi hydrogen pressure. The platinum catalyst is filtered off and the ethanol removed under vacuum. The residue is dissolved in ether and the ether solution washed several times with water to remove the excess 1,3-diaminopropane. The ether extracts are dried over anhydrous sodium sulfate and concentrated under vacuum to leave the diamine product, 1-[1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,5-diazapentane.

Aufarbeitung

  1. concentrationThe cooled solution is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in ethanol and hydrogenated with PtO2 at room temperature
  3. filtrationThe platinum catalyst is filtered off
  4. customthe ethanol removed under vacuum
  5. dissolutionThe residue is dissolved in ether
  6. washthe ether solution washed several times with water
  7. customto remove the excess 1,3-diaminopropane
  8. dry with materialThe ether extracts are dried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4444781ecc344d81b16335c4fb2d12f8
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04139559

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