Abstract
The condensation product of adamantan-1-amine with formaldehyde, 1,3,5-tri(1-adamantyl)-1,3,5-triazacyclohexane, was treated with three different types of ketones: symmetric (RCH2)2CO, nonsymmetric RCH2COCH3, and acetone to obtain 1,5-R-N,N′-di(1-adamantyl) bispidin-9-ones, N,N′-di(1-adamantyl)-1-[(1-adamantylamino)methyl]-5-methylbispidin-9-one, and N,N′-di(1-adamantyl)-1,5-bis[(1-adamantylamino)methyl]bispidin-9-one. 1,5-R-N,N′-Di(1-adamantyl)bispidin-9-ones were reduced with sodium borohydride to 1,5-R-N,N′-di(1-adamantyl)bispidin-9-ols.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1110–1113, June, 2018.
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Kuznetsov, A.I., Senan, I.M., Alasadi, R.T. et al. Synthesis of N,N′-di(1-adamantyl)bispidin-9-ones. Russ Chem Bull 67, 1110–1113 (2018). https://doi.org/10.1007/s11172-018-2189-1
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DOI: https://doi.org/10.1007/s11172-018-2189-1
Key words
- adamantan-1-amine
- amantadine
- 3,7-diazabicyclo[3.3.1]nonane
- bispidine
- 1,5-disubstituted 3,7-di(1-adamantyl)-3,7-diazabicyclo[3.3.1]nonan-9-ones
- 1,5-disubstituted 3,7-di(1-adamantyl)-3,7-diazabicyclo[3.3.1]nonan-9-ols
- 3,7-di(1-adamantyl)-1-[(1-adamantylamino) methyl]-5-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one
- 1,5-bis[(1-adamantylamino) methyl]-3,7-di(1-adamantyl)-3,7-diazabicyclo[3.3.1]nonan-9-one
- 1,5-disubstituted N,N′-di(1-adamantyl)bispidin-9-ones
- N,N′-di(1-adamantyl)-1-[(1-adamantylamino)methyl]-5-methylbispidin-9-one
- N,N′-di(1-adamantyl)-1,5-bis[(1-adamantylamino)methyl]bispidin-9-one.