Hydrochloric Acid → HCID 18705606, compound

Temperature

60 °C

3,6,9,12,18-Pentaazabicyclo[12.3.1]octadeca-1(18),14,16-trien-2,13-dione prepared as in Example 38A (1.0 g, 3.6 mmol) was dissolved in methanol (75 ml) and concentrated hydrochloric acid (2.14 g, 21.7 mmol) was added, then the catalyst platinum dioxide hydrate (0.5 g, 2 mmol). The mixture was heated to 60° C. and hydrogenated at 60 psi for 24 h. A white crystalline solid formed during the hydrogenation. The reaction mixture was filtered, and the precipitate was washed with water to dissolve it. The filtrate was concentrated to remove the alcohol and sodium hydroxide (1.0 N) was added to raise the pH to 11. This solution was extracted five times with dichloromethane (75 ml each), the solvent was removed under reduced pressure, and the resulting white solid was dried on the vacuum line to give 0.74 g (73% yield) of product: mp 193-195.5° C. (dec); 1H NMR (CD2Cl2) δ 0.79-1.48 (several m, 5 H), 1.88 (m, 2 H), 2.01 (m, 2 H), 2.63-2.88 (several m, 8 H), 3.10 (m, 2 H), 3.24 (m, 2 H), 3.36 (m, 2 H), 7.71 (s, 2 H).

1. customA white crystalline solid formed during the hydrogenation
2. filtrationThe reaction mixture was filtered
3. washthe precipitate was washed with water
4. dissolutionto dissolve it
5. concentrationThe filtrate was concentrated
6. customto remove the alcohol and sodium hydroxide (1.0 N)
7. additionwas added
8. temperatureto raise the pH to 11
9. extractionThis solution was extracted five times with dichloromethane (75 ml each)
10. customthe solvent was removed under reduced pressure
11. customthe resulting white solid was dried on the vacuum line

ORD record

ord-95274746cde54d5e9feabf94231929b7

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06084093