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| | 3,8-Diaza-bicyclo[3.2.1]octane
Basic information |
| | 3,8-Diaza-bicyclo[3.2.1]octane
Chemical Properties |
| Boiling point | 78-80 °C(Press: 40 Torr) | | density | 0.975±0.06 g/cm3(Predicted) | | pka | 10.32±0.20(Predicted) |
| | 3,8-Diaza-bicyclo[3.2.1]octane
Usage And Synthesis |
| Chemical Properties | A colorless fluid boiling 178-180° with piperazine-like smell, which quickly adsorbs carbon dioxide
when exposed to air.[2] | | Uses | The ring-system of 3,8-Diaza-bicyclo[3.2.1]octane is at once related to piperazine and to nortropine, both progenitors of many compounds of physiological importance, synthesis of 3,8-Diaza-bicyclo[3.2.1]octane seemed likely to be rewarding.[1]
| | Synthesis | From 3-bentyl-3,8-diazabicyclooctane[3.2.1] (V). A solution of 20 g of 3-benzyl-3,8-diazabicyclooctane [3.2.1] in 400 ml of absolute ethanol
was hydrogenated in the presence of 10 g. of 10% palladium
on charcoal in an autoclave at 60° and 40 atm. pressure.
After 3 hr., heating was stopped and the solution allowed
to cool to room temperature. Then the catalyst was filtered
off, the alcohol removed at atmospheric pressure, and the
concentrated solution was distilled; yield 8.8 g. of 3,8-Diaza-bicyclo[3.2.1]octane (80%) ;
b.p. 176-178'. The product easily adsorbed carbon dioxide
when exposed to air. A sample was distilled again and the
fraction boiling at 78-80°/40 mm. was collected and immediately analyzed.[2]
![3,8-Diaza-bicyclo[3.2.1]octane synthesis](/NewsImg/2025-12-10/6390096116866245976533513.png "3,8-Diaza-bicyclo[3.2.1]octane synthesis")
| | References | [1] SAMUEL W. BLACKMAN RICHARD B. The Synthesis of 3,8-Diazabicyclo[3.2.1]octane and Some of Its N-Substituted Derivatives[J]. The Journal of Organic Chemistry, 1961, 26 8: 2750-2755. DOI:10.1021/jo01066a032.
[2] GIORGIO CIGNARELLA EMILIO O GIANGIACOMO NATHANSOHN. Bicyclic Homologs of Piperazine. II. Synthesis of 3,8-Diazabicyclo[3.2.1]octane. New Synthesis of 8-Methyl-3,8-diazabicyclo[3.2.1]octane[J]. The Journal of Organic Chemistry, 1961, 26 8: 2747-2750. DOI:10.1021/jo01066a031. |
| | 3,8-Diaza-bicyclo[3.2.1]octane
Preparation Products And Raw materials |
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