1,3-Propanediamine → Benzyl (3-aminopropyl)carbamate

HRID 5555

Reaktionsgleichung

Reaktionsgleichung von HRID 5555
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[CH2:6]([O:13][C:14](ON1C(=O)CCC1=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[CH2:6]([O:13][C:14]([NH:1][CH2:2][CH2:3][CH2:4][NH2:5])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 4281,3-PropanediamineHCID 83172Benzyl succinimido carbonate

Produkt 1

HCID 417669Benzyl (3-aminopropyl)carbamateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1,3-Diaminopropane (35.5 g, 0.48 mol) was dissolved in 300 mL CHCl3, and the solution was cooled to 0° C. A solution of N-(benzyloxycarbonyloxy)succinimide (4.5 g, 0.018 mol) in 150 mL CHCl3 was added dropwise over 6 h, with the internal temperature maintained below 10° C. After addition was complete, the reaction solution was stirred at room temperature overnight. The solution was washed with water, dried (Na2SO4), filtered and concentrated in vacuo to provide 3.0 g (80%) of the title compound as a low melting solid: 1H NMR (CDCl3) δ 1.25 (bs, 2 H), 1.63 (quintet, 2 H), 2.77 (t, 2 H), 3.2-3.34 (bm, 2 H), 5.09 (s, 2 H), 5.37 (bm, 1 H), 7.28-7.40 (m, 5 H); MS, m/e 209 ((M+H)+).

Aufarbeitung

  1. temperaturemaintained below 10° C
  2. additionAfter addition
  3. washThe solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ef05d718e3f423da6bae4217b5ff8bd
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244910

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