CS200148B1 - Substituted n-(4-/phenoxy/butyl)piperidin-n-oxides and process for preparing them - Google Patents

Description

The invention relates to substituted 1- (4- (phenoxy) butyl) piperidine-N-oxides of the general formula

O - | C _{2 2 4} -0.

R wherein R is: ortho-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl, cyclohexyl; methoxy; para-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl, cyclohexyl, tert. octyl, n-nonyl and chloro and a process for their preparation. Amine oxides are also of significant industrial use. They are used as detergents and surfactants, foam stabilizers, antioxidants, antimicrobial agents, carcinostatics, etc. The compounds of the present invention have hitherto unknown effects on B.subtilis and S, aureus, whose antimicrobial activity was higher or comparable with disinfectants currently used in our country.

The amine oxides can be prepared in several ways, most preferably oxidation with hydrogen peroxide. The novel compounds are prepared by a process according to the invention which comprises oxidizing the corresponding tertiary amine - substituted N- (4- (phenoxy) butyl) piperidine / the meaning of the substituents is the same as above / - 30% aqueous hydrogen peroxide solution in methanol at 60 ° C for 3 hours. Oxidation generally has the advantage over other methods for the preparation of amine oxides that they produce products in high yield, high purity, using only a small amount.

The amount of solvent and the reaction time is substantially shorter compared to other methods for the preparation of amine oxides.

To illustrate the preparation method as well as some physical constants, the following examples are given.

Example 1

To a solution of 0.1 mol of N- (4- (o-methylphenoxy) butyl) piperidine in 20 ml of methanol at 60 ° C was added 0.12 mol of a 30% aqueous solution of hydrogen peroxide. After addition of the oxidizing agent, the mixture is allowed to react for a further 3 hours. After decomposition of excess hydrogen peroxide, evaporation of water and solvent, the crude product is recrystallized several times to a constant melting point. The yield of N- (4- (o-methylphenoxy) butyl) piperidine-N-oxide is 87%, m.p. 115-116 ° C, elemental analysis (calculated / found X):? = 72.97 / 73.18, H = 9.57 / 9.75,? = 5.32 / 4.99, = 219.273 nm.

ΙΙαΧ

Example 2

The procedure is the same as in Example 1, but N- (4- (m-methoxyphenoxy) butyl) piperidine was used for the oxidation. Yield: 88%, m.p. 102-103 ° C, elemental analysis (calculated / found X): δ = 68.79 / 68.69, H = 9.02 / 9.00, M δ 5.01 / 4.98, 221 221.277 nm.

Example 3

The procedure is the same as in Example 1, but N- (4- (p-butylphenoxy) butyl) piperidine was used for the oxidation. The product yield is 87%, mp 116-117 ° C, elemental analysis (calculated / found X): 0 = 74.71 / 74.58, H = 10.23 / 10.42 ¹ , N = 4.58 / 4 , 41, ^λ ββ ^χ 225.279 nm.

Example 4 The working procedure is the same as in Example 1, but N- (4- (o-sec. Butylphenoxy) butyl) piperidine was used for the oxidation. Yield: 84%, m.p. M.p. 101-102 ° C, elemental analysis (calculated / found X): 0 = 74.71 / 74.68, B * 10.23 / 10.35, N = 4.58 / 4.45, λ * 218.272 nm.

DHx

Example 5

The procedure is the same as in Example 1, but using N- (4- (p-tert.

butylphenoxy) butyl) piperidine. The product yield is 85% as an oil, elemental analysis (calculated / found X) 10 = 74.71 / 74.50, H = 10.23 / 10.28, N = 4.58 / 4.52, Λ " = 225.277 nm.

H (* x

Example 6

The operating procedure is the same as in Example 1, but N- (4- (o-phenylphenoxy) butyl {piperidine) is used for the oxidation, yield 90%, m.p. ; 0 = 77.50 / 77.43, H = 8.37 / 8.40, Ν = 4.3β / 4.27, λ _χχ 212.248 nm.

200 148

Example 7

The procedure is the same as in Example 1, but N- (4- (p-chlorophenoxy) butyl) piperidine was used for the oxidation. The product yield is 81%, m.p. 136-140 ° C, elemental analysis (calculated / found%): 0 = 63.65 / 63.89, H = 7.83 / 8.01, N = 4.94 / 4.78, = 229.283 nm.

max

Example 8

The procedure is the same as in Example 1, but N- (4- (p-n-nonylphenoxy) butyl) piperidine was used for the oxidation. The yield of the product is 83%; mp 93-96 ° C; elemental analysis (calculated / found%): 0 = 76.75 / 76.50, »= 11.00 / 11.29, N = 3.73 / 3.80, _Λβχ = 225.276 nm.

OBJECT OF THE INVENTION

Claims (2)

OBJECT OF THE INVENTION Substituted N- (4- (phenoxy (butyl) piperidine-N-oxides) of the general formula O> O- | CH ₂ |, .hQ. R where R represents: ortho-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl, cyclohexyl or methoxy-or para-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl , cyclohexyl, tert-octyl, n-nonyl and chloro. 2. A process for the preparation of compounds according to claim 1, characterized in that the substituted N- (4- (phenoxy, butyl) piperidine of the formula I) is oxidized. Wherein R is as defined in point 1, with a 30% aqueous solution of hydrogen peroxide at 60 ° C for 3 hours in methanol.