UA125219U - 1 ', 7-DIBENZYL-2,4-DIOXO-1H, 5H-SPYRO [3,7-DIAZABICYCLO- [3.3.1] NONAN-9,4'-PIPERIDINE] -1,5-DICARBONITRYL - 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.

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 | Soizepko M.M., KtgimoKoiuzKo 5.0., I ymipom M.R.

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

M.M., KimoKoiuzKo 5.S., | by M.R. Mopaiz5K Spet. 2007, 138, 489; Boizepko M.M., KiimoKoiuzkKo 5.0., Pymipom M.R. Option 55. Spent You, Iyi. 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., Ooivzepko

M.M. Spent Self-employed. motherfucker 2012, 48, 1722 (Chemistry of heterocycles. United 2012, 1838);

Egoiom K.A., OoivepKo MM, KimoKkoiuvzKo 5.S1., | Pmipom M.R. Spent Self-employed. Sotra 2012, 48, 442 (Chemistry of heterocyclic compounds 2012, 471); OoizepKo M.U., EgoYiom K.A., KgimoKoiuzKo 5.2. 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); YuoibepKo M.M., EgoYiom K.A., KypmoKoiuzKo 5.6., Spidoppa 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, 5H-spiro|3,7-diazabicycloi|3.3.1|-nonane-9,4"-piperidine| -1,5-dicarbonitrile (1).

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

M

Mo

SM

M (c) nm (c) 1,7-Dibenzyl-2,4-dioxo-1H,5H-spiro3,7-diazabicyclo|3.3.1|nonane-9,4-piperidine-1,5-dicarbonitrile (I) (yield 59 95) is obtained as follows: up to 20 ml of 96 95 ethanol

Add 2.2 mmol of benzylamine and 26.6 mmol of 37 95 formalin. 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 is added (Khi, U.; Hie, I.. ; Nap, V.; Maupaga, .0.; Spepaga, V.Y..;

Ziaar, A.). Raiepi MMO2009097405| 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 reaction mass is treated with 0.6 ml (1 mmol) of 1095 KOH, then boiled for 1 minute and filtered through a pleated paper filter. After 24 hours, the crystalline precipitate is filtered off and 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 - TMS), NMR spectra of "ZS" were recorded on the "VhyKkeg Amapse Sh HO" device (100 MHz in DMSO-av (internal standard - TMS) ). IR spectra were obtained on an IKS-29, LOMO spectrophotometer in petroleum jelly. Elemental analysis was performed on a RegKip-EIteg C, H, M-Apaii2e device.

Control of the individuality of the obtained compound was carried out by the TLC method on plates "ZYSHTOI!

OM-254", in the acetone-heptane system (1:1), development - iodine vapor, IR detector. The melting point was determined on a Kofler table and was not corrected.

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

1,7-Dibenzyl-2,4-dioxo-1H,5H-spiroi3, 7-diazabicyclo-I3.3.1|nonane-9,4-piperidine-1,5-dicarbonitrile (I), white fine crystalline powder, m.p. . 248-250 "S. IR spectrum, m, cm"!: 3412, 3185 (MN), 2250 (S-M), 1738, 1710 (S-O). NMR spectrum of "H" (Fig. 1 - NMR spectrum of "P 1",7-dibenzyl-2,4-dioxo-1H,5H-spiro|3,7-diazabicycloY3.3.1|-nonane-9,4"-piperidine| -1,5-dicarbonitrile (I), b, m. 00 h. (U), Hz): 1.90-1.96 (2H, m, CH"); 2.16-2.22 (2H, m, CH»e); 2.64-2.70 (2H, m, CH); 2.71-2.75 (2H, m,

SN"); 3.01 (2H, d, 29U-11.8) and 3.19 (2H, d, 22-11.8, 6,8-CH»e); 3.52 (2H, ear. c, (M-1)СНеРН); 3.69 (2H, ear. c, (M-7)СНеРН); 7.15-7.18 (2H, m, H RI); 7.24-7.32 (8H, m, H RI); 12.58" (1Н, с, МН). х|Integral intensity reduced due to partial deuterium exchange. NMR spectrum of "ZS" (Fig. 2 - NMR spectrum of "ZS 1",7-dibenzyl-2,4-dioxo-1H,5H-spiro |3,7-diazabicyclo|3.3.1|-nonane-9,2-piperidine-1,5-dicarbonitrile (I)), b, m.p.: 27.4; 28.7; 28.9; 32.7; 36.9; 47.4; 47.7; 52.1; 52.7; 58.3; 61.6; 116.6 (S-M); 127.0 (0-4 RI); 127.6 (0-4 RI); 128.2 (2C RI); 128.3 (2C RI); 128.5 (2C RI); 128.6 (2C RI); 136.3 (0-1 PH); 138.0 (0-1 RI); 167.0 (S-O). Found, 95: С 71.64; H 6.11; M 15.39.

С27Н27М5О". Calculated, 905: С 71.50; H 6.00; M15.44.

Claims (1)

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