UA125220U - 1 ', 7-DIBENZYL-2,4-DIOXO-1H, 5H-SPYRO [3,7-DIAZABICYCLO- [3.3.1] NONAN-9,4'-PIPERIDINE] -1,5-DICARBONITRYL HYDROGEN CHLORIDE - Google Patents

Abstract

1 ', 7-Dibenzyl-2,4-dioxo-1H, 5H-spiro [3,7-diazabicyclo [3.3.1] nonane-9,4'-piperidine] -1,5-dicarbonitrile hydrogen chloride.

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|Inonan |Ooizepko M.M., KiimoKoiuzKo 5.(23., I ymipom M.R.

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

M. M., KpimoKkoiuzKo 5. a., I ymipom U. R. Mopaiba. Snet 2007, 138, 489; boyzepKo MU.U., KpimoKoiuzko 5.0., I ymipom M.R. Ex. 5 Spent Yeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee Ed. 2007, 56, 2482 (Izv. AN. Ser. Chem. 2007, 2397);

SNidogipa E.A., EGgoYom K.A., YuoizepKo MU.U., SoYomevnKip A.5., Vybptagipom 1I.5., KimoKoiuzKo 5.0.

Ex. 5 Spent Howl, Yippee. Ed. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260); Spidogipa E.A., OoivepCo

M.M. Spent Self-employed. Sotra 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); EgoYom

KA., Yuoizepko M.M., KtimokoiuzKo 5.6., I ympom M.R. Spent Self-employed. motherfucker 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); BoizepKko U.M., EgoYom K.A., KtimokoiuzKo 5.0. Spent

Self-employed. motherfucker 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); YuBoisepKo M.M.,

KimoKoiubzKo 5.2., I ymipom, M.R. Spent Self-employed. motherfucker 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); YuOizepKo M.M., Egoiom K.A., KgimoKoiubieKo 5.0., Spidogipa E.A,.,

ReKpiegema T.M., Bnukom 5.My., Rarauapipa E.5., YuOtishmepKo A.O., VybzPtagpom 1.5. Spent

Self-employed. Sotra 2016, 52, 116 (Chemistry of heterocyclic compounds 2016, 52, 116)).

A common essential feature of the analogs and the claimed utility model is that these compounds contain a basic structure of 3,7-diazabicyclo/3.3.1|nonane.

The useful model, unlike its analogues, contains an oxygen atom in its composition instead of sulfur and selenium or a co-connected fragment in the case of its oxygen-containing analogues.

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

In accordance with this, a new compound is proposed in the useful model - 1',7-dibenzyl-2,4-dioxo-1H, BN-spiro|3,7-diazabicycloi3.3.1|-nonane-9,4"-piperidine-1, 5-dicarbonitrile hydrogen chloride (1).

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

SI:

M on

Mo

SM

M (c) nm (c) 177-Dibenzyl-2,4-dioxo-1H, 5H-spiroyi3,7-diazabicycloY3.3.1|nonane-9,4-piperidine-1,5-

Hydrogen chloride (I) (yield 55 95) is obtained from dicarbonitrile as follows: 2.2 mmol of benzylamine and 26.6 mmol of 37 95 formalin are added to 20 ml of 96 95 ethanol. The solution is stirred at room temperature for 1 hour, 1 mmol of 9-benzyl-2,4-dioxo-3,9-diazaspiro|5.5)undecane-1,5-dicarbonitrile IXhy, M. is added; Hie, Y.; Nap, V.; Maupaga, village 0.;

Snepaga, V.I.; Yeiaab A.). Raiepi UMO20090974051 and 2-3 drops of triethylamine, boil the resulting mixture for 2 minutes and quickly filter through a pleated paper filter. After 12 hours, excess hydrochloric acid is added dropwise to pH b. The precipitate obtained is filtered, washed with ethanol.

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

IR spectra taken on the "Vhykeg OEH-500 (500 MHz)" device in DMSO-av (internal standard - TMO), IR spectra were obtained on the IKSO-29, LOMO spectrophotometer in petroleum jelly. Mass spectra were recorded on a liquid chromatograph "Adiepi 1100" with detectors "AYU, EI! 5O bedeh 75", combined with the mass spectrometer "Adipiepi I S/M5O MI", ionization - electrospray.

Elemental analysis was carried out on the device "RegKip-Eiteg S, H, M-Apaii2eg". Control of the individuality of the obtained compound was carried out by the TLC method on "ZiishShoY OM-254" plates, 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

17-Dibenzyl-2,4-dioxo-1H,5H-spiroyi3,7-diazabicyclo-(3.3.1|nonane-9,4-piperidine-1,5- dicarbonitrile hydrogen chloride (I), white fine crystalline powder, T.pl . 272-274 76. IR spectrum, m, cm": 3480, 3378, 3258, 3190 (MH), 2250 (С-М), 1743, 1710 (С-О). NMR spectrum "НН, b, m (U, Hu: 2.08-2.38 (AN, m), 2.83-2.95 (1Н, m), 3.02-3.08 (2Н, m) and 3.09-3.18 (1Н, m, 4СН»); 3.27 (IN , d, 20-11.0), 3.35 (1H, d, 2)-11.0), 3.35 (1H, d, 29-11.0) and 3.54 (1H, d, 2)-11.0, 8-CH» or 6-

SN"); 3.69 (2H, sh. s, MSNORI); 4.31 (2H, sh. s, ""MNONERN); 7.14-7.16 (2H, m, H RI); 7.28-7.33 (ZN, m, H RI); 7.42-7.46 (ZN, m, H RI); 7.57 -7.61 (2H, m, H RI); 11.39 (1H, sh. s, "MN); 12.78 (1Н, с, МН).

Mass spectrum, t/2. 454 |M-SITS", 452 |M-SI-NI. Found, 90: So - 66.06; H - 5.89; M-14.20.

C27NgvSIM5O". Calculated, 90: C - 66.18; H - 5.76; M-14.29.

Claims (1)

USEFUL MODEL FORMULA 1,7-Dibenzyl-2,4-dioxo-1H,5H-spiro3,7-diazabicyclo|3.3.1|nonane-9,4-piperidine-1,5- dicarbonitrile hydrogen chloride: SI- M yan Mo SM M (c) NM (c)