Heating of 3,7 di(tert butyl) 1,5 dimethyl 3,7 diazabicyclo[3.3.1]nonan 9 one with hydro bromic acid gave 1,5 dimethyl 3,7 diazabicyclo[3.3.1]nonan 9 one (1,5 dimethylbispidin 9 one). Condensation of this compound or 1,5 dimethylbispidin 9 ol with dialdehydes afforded new compounds containing two 1,3 diazaadamantane moieties in one molecule, which are connected either directly or through spacers.Key words: bispidines condensation, 1,5 dimethyl 3,7 diazabicyclo[3.3.1]nonan 9 one, 1,5 dimethylbispidin 9 one, dialdehydes, bi(1,3 diazaadamantan 6 one).It is known that bispidines possess pronounced biolog ical activity 1-4 and, besides, are of practical interest as complexation agents with metal salts. 5-8 Earlier, 9 we used the condensation of 1,3,5 tri(tert butyl) 1,3,5 triaza cyclohexane with diethyl ketone to obtain 3,7 di(tert butyl) 1,5 dimethyl 3,7 diazabicyclo[3.3.1]nonan 9 one (N,N´ di(tert butyl) 1,5 dimethylbispidin 9 one, 1) in 72% yield. The choice of the tert butyl group as a substitu ent at the nitrogen atoms is explained by a possibility of its further removal. 10 In the present work, we report the synthesis of 1,5 di methyl 3,7 diazabicyclo[3.3.1]nonan 9 one (2a) 11 by heating of bispidinone 1 with hydrobromic acid for 30 min and subsequent alkalization of the reaction mix ture (Scheme 1). The yield of the reaction product 2a was 54%.aaa 1,5 Dimethylbispidinone 2a was reduced with sodium boronhydride to 1,5 dimethyl 3,7 diazabicyclo[3.3.1] nonan 9 ol (1,5 dimethylbispidin 9 ol, 2b) 12 in 68% yield (see Scheme 1).Literature data show that the reaction of bispidines with carbonyl compounds can be used in the synthesis of 1,3 diazaadamantane derivatives. 13 A possibility of such condensation is provided by the closeness of the NH groups in the chair chair conformation of bispidine. In the case of 1,5 disubstituted bispidines, the absence of steric hin drance and the high reactivity of the NH groups make it possible to use a wide range of carbonyl compounds in this condensation. Thus, a series of 2,2 disubstituted 5,7 dis ubstituted 1,3 diazaadamantanes were obtained by the re action of 1,5 disubstituted bispidines with various aliphatic and aromatic aldehydes or aliphatic ketones. 10,14-16In the last years, in organic chemistry an interest is growing to the preparation of enlarged molecules with new or improved properties via their synthesis from bi and polyfunctional molecules. 3,17, 18 We for the first time synthesized the systems 3-6 with low molecular weights containing two 1,3 diazaadamantane fragments with high yields (Scheme 2).We found that such products are formed by the con densation of 1,5 dimethyl substituted bispidines 2a,b with various dialdehydes upon reflux in isopropyl alcohol. Scheme 1i. 1) HBr, 2) NaOH; ii. NaBH 4 , EtOH.

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Condensation of 1-(pyridin-4-yl)propan-2-one with 1, 3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane gave 1-( pyridin-4-yl)-3,6-diazahomoadamantan-9-one as intermediate product in the synthesis of 1-(pyridin-4-yl)-3,6-diazahomoadamantane and its derivatives having functional substituents at the bridging carbon atom in the homoadamantane skeleton.We previously [1] developed a procedure for the condensation of methyl ketones with 1, 3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane, which ensured synthesis of 3,6-diazahomoadamantane derivatives substituted at the bridgehead position [2-5]; Wolff-Kishner reduction of the latter gave a number of 3,6-diazahomoadamantane derivatives having aliphatic and aromatic substituents. No analogous compounds with heteroaromatic substituents were reported. We synthesized 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-one (II) using 1-(pyridin-4-yl)propan-2-one (I) as initial methyl ketone; it was prepared by acylation of 4-methylpyridine with acetyl chloride according to the procedure described in [6]. The condensation of ketone I with 1, 3,6,8-tetraazatricyclo[4.4.1.1 3,8 ]dodecane gave compound II in more than 40% yield (Scheme 1).The structure of 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-one (II) was confirmed by spectral data. Its 1 H NMR spectrum contained a set of signals typical of diazahomoadamantane skeleton. It included two AB systems arising from the NCH 2 C protons, a multiplet from the ethylene fragment (NCH 2 CH 2 N), and a broadened singlet from one proton in the bridgehead position. Protons in the pyridine ring resonated as two symmetric doublets in the region δ 7.11-8.25 ppm. In the IR spectrum we observed an absorption band at 1695 cm -1 due to stretching vibrations of the carbonyl group. Compound II displayed the molecular ion peak (m/z 243) in the mass spectrum.Ketone II was converted into the corresponding hydrazone III, and the latter was reduced according to Wolff-Kishner to obtain 1-(pyridin-4-yl)-3,6-diazahomoadamantane (IV) in 76% yield. Heating of hydrazone III with alkali was accompanied by formation of a considerable amount of 4-(3,6-diazahomoadamantan-1-yl)pyridin-2-ol (V). The IR spectrum of IV lacked absorption band assignable to stretching vibrations of C=N bond (which is typical of hydrazone III). Absorption bands belonging to vibrations of the pyridine ring were observed at 1590 and 1530 cm -1 . By reduction of II with NaBH 4 we obtained 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-ol (VI), and acylation of VI afforded 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-yl acetate (VII). In the IR spectrum of VII we observed no absorption band at 3203 cm -1 typical of stretching vibrations of the OH group in initial alcohol VI, and ester carbonyl band appeared at 1730 cm -1 .1-(Pyridin-4-yl)-3,6-diazahomoadamantan-9-amine (IX) was synthesized by reduction of 1-(pyridin-4-yl)-3,6-diazahomoadamantan-9-one oxime (VIII) with

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