UA125224U - 7-BENZYL-9,9-DIMETHYL-2,4-DIOXO-3,7-DIAZABicyclo [3.3.1] NONAN-1,5-DICARBONITRYL - Google Patents

Abstract

7-Benzyl-9,9-dimethyl-2,4-dioxo-3,7-diazabicyclo [3.3.1] nonane-1,5-dicarbonitrile EMBED ISISServer.

Description

A useful model belongs to the field of organic synthesis, namely to new derivatives of piperidine, which may find their application as compounds with directed pharmaceutical action or "building blocks" for obtaining new valuable organic compounds.

The products of aminomethylation of imides are closest to the claimed compound

Guareski - derivatives of 3,7-diazabicyclo|3.3.1|nonane (OoizepKo U. U., KiimoKoiuzKo 5. a., Iimipom U. R.

Spent Self-employed. motherfucker 2005, 41, 1428 (Chemistry of heterocyclic compounds 2005, 1695); BoivepCo

M. M., KimoKoiuzKo 5. (1., I ymipom M. R. Mopaibvn. Spet. 2007, 138, 489; RoyvepKo M. UM.,

KiimokoiuzKo 5. S., I ymipom M. R. Vy55. Spent Howl, Yippee. Ed. 2007, 56, 2482 (Izv. AN Ser. chem. 2007, 2397); SPidogipa E. A., Ertoyom K. A., Yuoivepko M. M., Soiome5zNnKip A. 5., VizPptagipom I. 5.,

KiimoKoiubzKo 5. S. NKyb55. Spent Yeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee Eh. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260);

Spidogipa E. A., YuOoizepko M. M. Spet. Neiegosusi Sotra. 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); Egoiom K. A., Yuoizepko U. M., KipimoKoiuzKo 5. S., I ymipom M. R. Snet.

Neiegosusi Sotra. 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); RoizepKko U.U.,

Egoiom K. A., KimoKoiiueKo 5. S. Spet. Neiegosusi Sotra. 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); Yuoivepko M. M., KimoKoiubKo 5. S., I Pmipom, M. R. Spet. Self-employed.

Sotra 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); Royvepko U. U., Yegoyom K. A.,

KiiimoKoiuzKo 5. a., Spidogipa E. A., ReKniegema T. M., Ztsukom 5. My., Rarauapipa E. 5., Otiiniepko

A. O., VizPtaiipom I. 5. Spet. Self-employed. Sotra 2016, 52, 116 (Chemistry of heterocyclic compounds 2016, 52, 116)|.

A common essential feature of the closest analogue and the claimed utility model is that these compounds contain the basic structure of 3,7-diazabicyclo|3.3.1|nonane (OABSM, bBigvriaipe).

The useful model, unlike the closest analogs, contains an oxygen atom instead of sulfur and selenium in its composition, which lacks aryl or co-connected fragments in the case of comparison with oxygen-containing analogs.

The task of a useful model is to create a new derivative of piperidine.

Accordingly, a new compound -7-benzyl-9,9-dimethyl-2,4-dioxo-3,7-diazabicyclo/3.3.1|nonane-1,5-dicarbonitrile (1) is proposed in a useful model.

Compound I and methods of obtaining it are not described in patent publications.

Me

Mo Me

SM

M (in) nm (in)

She

7-Benzyl-9,9-dimethyl-2,4-dioxo-3,7-diazabicyclo|3.3.1|nonane-1,5-dicarbonitrile (I) (output 1995) is obtained as follows: mix a suspension of 4,4- of dimethyl-3,5-dicyano-2,6- piperidindione (Guareschi imide) (Scagezsny I. Spet. 2BI, 1901, I, 579; Stsagezsny I. Sa. Spit. MO., 1919, 49 (1), 126; Napaieu S.U., Meivop E.V., Botegv T.O. A!yvig, U.Spet., 1960, 13, 129) (1.0 mmol) in 96 95 ethanol (20 ml), triethylamine (2 -3 drops), benzylamine (2.2 mmol) and 37 95 solution of formaldehyde (formalin) (2.0 ml, 26.6 mmol). The mixture is stirred for 1 minute, boiled for 2 minutes, the resulting solution is filtered through a paper pleated filter. After 12 hours, the mixture is acidified with hydrochloric acid to pH 6.0, kept at room temperature for two hours, the precipitate is filtered, washed with ethanol, the product is recrystallized from an acetone-ethanol mixture (1:1).

The structure of the compound obtained as a result of the reaction is confirmed by NMR spectra

IN, taken on the device "Vhykeg OV8X-500 (500 MHz)" in DMSO-AV (internal standard - TMS); IR spectra were obtained on a spectrophotometer "IKO-29, LOMO" in petroleum jelly. Mass spectra were recorded on an Adiepi 1100 liquid chromatograph with OAO, EII5O bBedekh 75 detectors, combined with an Adiepi I S/M5O MI mass spectrometer, ionization - electrospray.

Elemental analysis was carried out on the device "ReiKip-EIteg S, H, M-Apaii2e!". Control of the individuality of the obtained compound was carried out by the TLC method on the plates of "Biishoy ShM-254", in the acetone-heptane system (1:11), development - iodine vapor, IR detector. The melting point was determined on a Kofler table and was uncorrected.

The resulting product has sufficient purity for analysis and for further use.

A useful model is confirmed by the following example, which illustrates, but does not limit its scope.

Example.

7-Benzyl-9,9-dimethyl-2,4-dioxo-3,7-diazabicyclo|3.3.1|nonane-1,5-dicarbonitrile (I), white fine crystalline powder, m.p. 246-248 "С; IR spectrum, о (cm"): 3407, 3171 (МН), 2262 (С.М), 1750, 1710 (С-О); "H NMR, 5 (ppm): 1.33 (s, ЗН, СН), 1.43 (s, ЗН, СН3), 3.05 (d, 2Н, 2920-11.5, Н- 6,

H-8), 3.16 (d, 2H, 2920-11.5, H-6, H-8), 3.70 (sh. s, 2H, SNeRNP), 7.15 (d, 2H, 50 -71, Н-2 Н-6 РН), 7.27- 7.32 (m, ЗН, Н-3, Н-4, Н-5 RI), 12.56 (w. s, 1Н, МН) ; Mass spectrum, t/2 (95): 91.2 (RISNAG, 323.1

IMaAT", 356.3 (Ma2MNz|, 321.1 (M-17. Calculated for StivNivMaO): C, 67.07; H, 5.63; M, 17.38. M - 322.37. Found: C , 67.13; H, 5.71; M, 17.34.

Thus, 7-Benzyl-9,9-dimethyl-2,4-dioxo-3,7-diazabicyclo-(3.3.1|nonane-1,5-dicarbonitrile (I) differs significantly in structural and physicochemical properties from compounds of comparison.

Claims (1)

USEFUL MODEL FORMULA 7-Benzyl-9,9-dimethyl-2,4-dioxo-3, 7-diazabicyclo|3.3.1|nonane-1,5-dicarbonitrile Me Mo Me CM M (c) ni Ge)