CS200149B1 - Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing - Google Patents

Description

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

R @ 1 denotes: ortho-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl cyclohexyl; methoxy; paratthyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl, cyclohexyl, tert-octyl, n-nonyl and chlorine, and methods for their preparation. As noted above, some piperidine derivatives exhibit biological properties, such as e.g. hypotensive, locally anesthetic, myorelaxant, antiadrenolytic effect, etc. However, the compounds of the present invention have not been prepared yet and are novel and not disclosed in the literature. They serve as. starting materials in the preparation of other biologically active compounds.

The novel compounds are prepared by the process of the invention, which comprises reacting the substituted 1-bromo-4-phenoxybutane (meaning substituents as above) with piperidine in boiling benzene for 6 hours. The process of the invention gives high yields, clean products and the process is simple.

To illustrate the preparation process as well as some physical properties, the following examples are given.

200 149

200 140

Example 1

While boiling, 0.1 mol of 1-bromo-4-o-methylphenoxybutane is added to 0.2 mol of piperidine dissolved in 150 ml of benzene and allowed to react for 6 hours. After cooling and filtering off the reaction mixture, the solvent was distilled off and the product was distilled off. N- (4- (o-methylphenoxy) butyl) piperidine is obtained in 77% yield, b.p. 143-145 ° C / 0.08 kPa, elemental analysis (calculated / found X): 0 = 77.68 / 77.71, H = 10.19 / 10.22, N = 5.66 / 5.49.

Example 2

The procedure is the same as in Example 1 except that 1-bromo-4-m-methoxyphenoxybutane was used as the alkylating agent. The product yield is 69%, b.p. 157-157.5 ° C / 0.05 kPa, elemental analysis (calculated / found X): 0 = 72.97 / 73.03, H = 9.57 / 9.50, N = 5.32 / 5, 41st

Example 3

The procedure is the same as in Example 1, using 1-bromo-4-p-butylphenoxybutane as the alkylating agent. The yield of the product is 68%, t 153 ° C / 0.03 kPa, η 1 = 1.5093, elemental analysis (calculated / found X): 0 = 78.84 / 78.90, H = 10.79 / 10.91.1 (= 4.84 / 5.00, - \ _ax => 225.279.285 nm).

«

Example 4

The procedure is the same as in Example 1, but 1-bromo-4-o-sec-butylphenoxybutene was used as the alkylating agent. The product yield is 56%, b.p. 140 ° C / 0.04 kPa, n 1 ° = 1.5096 elemental analysis (calculated / found X): 0 = 78.84 / 78.75, H = 10.79 / 10.71, N = 4.84 [.Alpha.] D @ 20 = 221.276 nm.

Example 5

The procedure is the same as in Example 1, using 1-brdm-4-p-tert-butylphenoxybutane as the alkylating agent. The product yield is 82%, t 162 ° C / 0.08 kPa, ηρ ° = 1.5128, electronic analysis (calculated / found X): 0 = 78.84 / 78.69, H = 10.79 / 10 , 87, N = 4.84 / 4.93, _Λβχ = 225.279 nm.

Example 6

The procedure is the same as in Example 1, using 1-brdm-4-o-phenylphenoxybutane as the alkylating agent. The product yield is 82%, b.p. 186-190 ° C / 0.03 kPa, elemental analysis (calculated / found X): δ = 81.51 / 81.73, H = 8.79 / 8.90, N 4,5 4.53 / 4.47.

Example 7

The procedure is the same as in Example 1, using 1-bromo-4-p-chlorophenoxybutane as the alkylating agent. The product yield is 71%, b.p. 156-158 ° C / 0.08 kPa, elemental analysis (calculated / found X): 0 = 67.33 / 67.19, H = 8.29 / 8.22, N = 5.23 / 5.44.

Example 8

The procedure is the same as in Example 1, using 1-bromo-4-p-n-nonylphenoxybutane as the alkylating agent. The product yield is 67%, b.p. M.p. 182-185 ° C / 0.03 kPa, elemental analysis (calculated / found%): 0 = 80.16 / 80.06, H 11, 49 / 11.55, R = 3.91 / 4.03.

Claims (2)

Substituted N- (4- (phenoxy) butyl) piperidines of the general formula 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 the compounds according to claim 1, which comprises reacting piperidine with a substituted 1-bromo-4-phenoxybutane of the formula: ## STR2 ## wherein R is as defined under 1 in a boiling benzene environment for 6 hours.