UA125218U - 1'-BENZYL-7- (1-METHYLPROPYL) -2,4-DIOXO-1H, 5H-SPYRO [3,7-DIAZABICYCLO [3.3.1] NONAN-9,4'-PIPERIDINE] -1,5-DICARBONITRIL - Google Patents

Abstract

1'-Benzyl-7- (1-methylpropyl) -2,4-dioxo-1H, 5H-spiro [3,7-diazabicyclo [3.3.1] nonane-9,4'-piperidine] -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 closest analogue is the aminomethylation products of Guareschi imides - derivatives of 3,7- diazabicycloY3.3.1|Inonane (M. OoizepKo, KimoKoiuzKo 5. S., Iimipom M. R. Spet. Neiegosusi.

Sotra 2005, 41, 1428 (Chemistry of heterocyclic compounds 2005, 1695); OoizepKo U. M., KimoKoiuzko

Z. b., GPmipom M. R. Mopaiva. Spent 2007, 138, 489; RoyvepKo U. M., KpimoKoiuvzKo 5. S., | ymipom M.

R. Ezv. Spent Howl, Yippee. Ed. 2007, 56, 2482 (Izv. AN Ser. chem. 2007, 2397); Spidoppa E. A., EgoYom

K. A., RoizepKo U. MU., SoomeznkKip A. 5., Vizptaipom I. 5., KimoKoiuzKo 5. S. Vyv5. Spent Howl, whoop.

Eh. 2016, 9, 2260 (Izv. AN. Ser. Chem. 2016, 2260); Spidogipa E. A., Yuoizepko M. M. Spet.

Self-employed. motherfucker 2012, 48, 1722 (Chemistry of heterocyclic compounds 2012, 1838); Egoio K. A.,

BoivepKko U. U., KimoKoiuzKo 5. a., and Pmipom U. R. Spet. Self-employed. Sotra 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); YuoizepKo M. M., Egoiom K. A., KgimoKoiuzKo 5. b. Spent

Self-employed. Sotra 2013, 49, 657 (Chemistry of heterocyclic compounds 2013, 705); OoizepKo U. M., KiimoKoiuzKo 5. (.,

Shimipom, M.R. Spet. Self-employed. Sotra 2015, 51, 109 (Chemistry of heterocyclic compounds 2015, 51, 109); boyzepKo UM. M., EgoYom K. A., KgimoKoiuzKo 5. O., Spidogipa E. A., Rekpnegema T. M, ZyTsukom 5.

Khy., Rarauapipa E. 5., OtinmiepkKo A. 0., VizPptagipom I. 5. Spet. Self-employed. Sotra 2016, 52, 116 (Chemistry heterocycle. connected 2016, 52, 116)|.

A common essential feature of the closest analogue and the useful model is that these compounds contain the basic structure of 3,7-diazabicycloΙ3.3.1|nonane.

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

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

In accordance with this, a new compound -1'-benzyl-7-(1-methylpropyl)-2,4-dioxo-1H, BN-spiro|3,7-diazabicyclo|3.3.1|-nonan-9 is proposed in a useful model ,4"-piperidine|-1,5-dicarbonitrile (1).

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

RA

Mo

CM zes vn, about 80 Nm o i 1-Benzyl-7-(1-methylpropyl)-2,4-dioxo-1H, 5H-spiro|3,7-diazabicyclo-I(3.3.1|nonane-9,4 "- piperidine-1,5-dicarbonitrile (I) (yield 62 95) is obtained as follows: 2.2 mmol of 1-methylpropylamine 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,-dicarbonitrile is added. Nap, V.;

Maupaga, village O0.; Spepaga, V. I.; Yeiaabr, A. u). Raiepi UUO20090974051 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 6.

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

IRs taken on the "Vhykeg OBH-500 (500 MHz)" device in DMSO-ydv (internal standard - TMO), NMR spectra of "ZS" were recorded on the "Magiap Opku Riiz (100.6 MHz)" device in SOSIz: DMSO-av (2 -1); 14 spectra were obtained on an IKOS-29, LOMO spectrophotometer in petroleum jelly. Mass spectra were recorded on an Adpepi 1100 liquid chromatograph with CAO, EI!5O BbBeidekh 75 detectors, combined with an Adpepi I S/M5O MI mass spectrometer, 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 "ZiishShoYi ShM-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 1-Benzyl-7-(1-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo-I(3.3.1|nonane-9,4"- piperidine|-1,5 -dicarbonitrile (I), white fine crystalline powder, mp 234-236 70. IR spectrum, m, cm"!: 3430, 3190 (MH), 2267 (С-М), 1730, 1708 (С-О) . NMR spectrum "H, b, m. h. (y, Hz): 0.68 (ZH, t, 390-7.2, СНоСН»); 0.90 (ЗН, d, 32-6.6, СНСН»); 1.16-1.25 ( 1H, m) and 1.30-1.41 (1H, m,

СНеНеСН»); 1.88-1.96 (2H, m, SNeg); 2.15-2.24 (2H, m, CH»e); 2.56-2.61 (1Н, m, СНИСНеСН»); 2.67-2.69 (2H, m, CH); 2.73-2.76 (2H, m, CH»e); 2.96-3.01 (2H, m), 3.15 (IN, d, M-11.8) and 3.42 (1H, d, 23-11.8, 6,8-СН»); 3.52 (2H, w. s, SNR); 7.23-7.27 (1H, m, H RI); 7.28-7.34 (4H, m, H RI); 12.48 (IN, s, MN). NMR spectrum of "С, 5, ppm: 10.6; 14.0; 25.7; 27.2; 32.9; 37.1; 47.1; 47.5; 47.6; 51.8; 52.6; 52.7; 59.2; 61.6; 116.8 (С-М); 127.0 (С -4 RI); 128.2 (2С RI); 128.7 (2С RI); 138.0 (С-1 РН); 167.2 (С-0); 167.3 (С-0). Mass spectrum, t/2: 420.2 MANI" , 418.2 |M-NO. Found, 90: C - 68.62; H - 6.99;

M-16.63. SgaNgoM5O". Calculated, 905: C - 68.71; H - 6.97; M-16.69.

Thus, 1-benzyl-7-(1-methylpropyl)-2,4-dioxo-1H,5H-spiroyi3,7-diazabicyclo/3.3.1|nonane-9,4"-piperidine|-1,5-dicarbonitrile (I) significantly differs from the comparison compounds in terms of structural and physico-chemical properties.

Claims (1)

USEFUL MODEL FORMULA 1-Benzyl-7-(1-methylpropyl)-2,4-dioxo-1H,5H-spiro|3,7-diazabicyclo/3.3.1|nonane-9,4-piperidine|- 1,5-dicarbonitrile: eh RP Mo -- SM zes Vi o nm (in)