SU1373707A1 - Method of producing 3,5,7-tribromo-1-azaadamantane - Google Patents

Description

(21) 4105912 / 23-04

(22) 08.08.86

(46) 02.15.88. Bul № 6

(71) Moscow Institute of Fine Chemical Technology. M.V.Lomonosova

(72) A.I. Kuznetsov and A.M. Beer (PL) (53) 547.834.1.07 (088.8)

(56) Speckamp W.N. Dekkers A.W.J.D. Tru - Radical Halogenation of 1 - Asa - Adamantane. - Tetrahedron Lett., 1974, No. 21, p. 1857.

(54) METHOD OF OBTAINING 3,5,7-TRIBROM--1-AZAADAMANTAN

(57) The invention relates to heterocyclic substances, in particular the preparation of 3.5,7g-tribrom-1-aza-admantane, an intermediate for the synthesis of active substances. The goal is to develop a new method of obtaining new intermediates. Synthesis of lead processing 3,5,7-triamino-1-azaadamantana NaNO in conc. HBg at 0–5 ° C, followed by neutralization and extraction of the target product with chloroform. Yield 32.7%, T.Sh1. 156-157 p.

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The invention relates to the study of azaadamantane derivatives, namely, 3,5,7-tribromo-1-azaadamantane, which can be used in the synthesis of biologically active substances.

The purpose of the invention is to develop a new method of obtaining a new compound 3,5,7-tribrom-1-azaadamantane.

Example 2. To a solution of 1 g of 3,5,7-triamino-1-aza-adamantane in 20 ml of 20% HBg, cooled to 0-5 C, with stirring for 10 30 MI, a solution of 1.8 g of nit is added sodium rita in 5 ml of water and continue stirring without cooling 2 more. The reaction mixture is worked up as in example 1 to obtain

Example 1. To a mixture of 1 g (5.5 mmol) of 3,5,7-triamino-1-azaadamantane and 10 ml of conc. PVG cooled to 0-5 ° C while stirring. B-15 °, 44 g (21.8%) 3,5,7-tribrom-1-application 30 minutes added a solution of 1.8 g adamantane. (26.1 mmol) of sodium nitrite in 4 ml of water and continue stirring without cooling for another 2 hours. The mixture is neutralized with a 40% alkali solution and extracted with chloroform (5-20 ml). Chloroform was distilled off, 10 ml of conc. HBg and heated at boiling for 2 hours. The acid is distilled off, the residue is triturated with potash and extracted. Thus, the proposed method allows to obtain previously unknown 3,5,7-tribromo-1-aza-admantane.

Claims (2)

Invention Formula 25 The method of producing 3,5,7-tribromo-1-aza-adamantane, characterized in that the 3,5,7-triamino-1-aza-adamantane is treated with sodium nitrite in concentrated hydrobromic acid at 0-5 With subsequent neutralization and extraction the target product is chloroform. Rut with chloroform (5-20 ml). The extract is passed through a thin layer of silica gel, the solvent is evaporated. The product is purified by sublimation. The output of 0.67 g (32.7%). M.p. 156-157 ° C. Found,%: C 28.90, H 3.23, N 3.70; Br 64.08, M 373. Calculated,%: C 28.91, H 3.23, N 3.75, Br 64.11, M 373.91. Example 2. To a solution of 1 g of 3,5,7-triamino-1-aza-adamantane in 20 ml of 20% HBg cooled to 0-5 ° C, while stirring for 30 MI, add a solution of 1.8 g of sodium nitrite in 5 ml of water and continue stirring without cooling for another 2 hours. The reaction mixture is treated in the same manner as in Example 1, and a o, 44 g (21.8%) 3,5,7-tribrom-1-aza-adamantane. o, 44 g (21.8%) 3,5,7-tribrom-1-aza-adamantane. Thus, the proposed method allows to obtain previously unknown 3,5,7-tribrom-1-aza-admantane. Invention Formula 15 o, 44 g (21.8%) 3,5,7-tribrom-1-aza-adamantane. 20 25 The method of obtaining 3,5,7-tribromo-1-aza-adamantane, characterized in that the 3,5,7-triamine-1-aza-adamantane is treated with sodium nitrite in concentrated hydrobromic acid at 0-5 With subsequent neutralization and extraction the target product is chloroform.