Reaktion #658776

ord-5fd45ad2e1874859bcba9fbdb89c970a

Reaktionsgleichung

[H][H]
hydrogen
CC(C)(CNCC(C)(C)[N+](=O)[O-])[N+](=O)[O-]
compound III
CC(C)(CNCC(C)(C)[N+](=O)[O-])[N+](=O)[O-]
Di-(2-nitroisobutyl)amine
[H][H]
hydrogen
[H][H]
hydrogen
→
CC(C)(N)CNCC(C)(C)N
Di-(2-aminoisobutyl)amine
Ausbeute 52.0%

Edukte

[H][H]
hydrogen
CC(C)(CNCC(C)(C)[N+](=O)[O-])[N+](=O)[O-]
compound III
CC(C)(CNCC(C)(C)[N+](=O)[O-])[N+](=O)[O-]
Di-(2-nitroisobutyl)amine
[H][H]
hydrogen
[H][H]
hydrogen

Reagenzien

[Ni]
Raney Nickel

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe solution filtered through celite
  2. 2
    Sonstigeto remove the catalyst
  3. 3
    SonstigeThe filtrate was evaporated under vacuum
  4. 4
    Sonstigeto remove all solvent
  5. 5
    workup.DISTILLATIONdistilled at room temperature
  6. 6
    Sonstigegiving a yield of 52%

Vorschrift

Into a 2 L pressure reactor, 21.17 g (0.0965 mol) of compound III was placed along with 600 mL of ethanol (90%). Approximately 3 g of Raney Nickel was added and the bomb was pressurized to 90 PSI with hydrogen (99.9%). The solution was stirred and intermittently repressurized with hydrogen. Over the course of 5 days, 105 PSI (0.406 mol) of hydrogen were consumed. The bomb was then depressurized and the solution filtered through celite to remove the catalyst. The filtrate was evaporated under vacuum to remove all solvent and then was vacuum distilled at room temperature and a pressure of 50 mtorr. Purified product weighed 8.031 g, giving a yield of 52%. Purity was checked by NMR, with a singlet at 2.26 ppm and a singlet at 0.96 ppm.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09029189B2uspto-grants-2015_05