7-Nitro-1,3,5-triazaadamantane → 1,3,5-Triazatricyclo[3.3.1.1,3,7]decan-7-amine

7-Nitro-1,3,5-triazaadamantane (46.1 g., 0.25 mole), 175 ml. of 95% ethanol and 8.0 g. of 5% rhodium-charcoal catalyst were shaken with hydrogen in a Parr apparatus at 25° until hydrogen uptake ceased (13 hours). (The reaction bottle was refilled with hydrogen at intervals as required to keep the hydrogen pressure between 25-50 psi.) The reaction mixture was filtered with suction through Celite and the collected catalyst washed thoroughly with ethanol. The filtrate was concentrated to dryness under reduced pressure and the solid residue, after being ground to a powder, was pumped at 25° and 0.1 mm for 12 hours to remove traces of volatiles to yield 38.6 g. (99.5%) of high purity 2, m.p. 216°-219°. The product may be recrystallized from benzene (80% recovery) to yield long needles, m.p. 214°-217°; nmr (deuterium oxide): δ 4.70 (2, s, OH), 4.39, 3.97 (6, ABq, J = 12 Hz; 2,4,9 CH2), 3.17 (6, s, 6,8,10 CH2); TMS external standard.

1. custom(13 hours)
2. filtration) The reaction mixture was filtered with suction through Celite
3. washthe collected catalyst washed thoroughly with ethanol
4. concentrationThe filtrate was concentrated to dryness under reduced pressure
5. customwas pumped at 25°
6. custom0.1 mm for 12 hours to remove traces of volatiles
7. customto yield 38.6 g
8. customThe product may be recrystallized from benzene (80% recovery)
9. customto yield long needles, m.p. 214°-217°

ORD record

ord-ca43551a73684940a70f71ac172333f7

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04012384