N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenox

Details N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenox N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenox

1993-11-03

1997-04-08

Nazario-Gonzalez, Porfirio

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 19, 560 24, 564347, 564348, 564351, C07C26906, C07C27136

Patent

active

056189680

ABSTRACT:
The invention provides the preparation procedure for N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine having the general formula (I), where R is hydrogen and the group of the general formula (II), in which R.sub.1 is aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, and n is 0 and 1, and also covers the compounds of the general formula (I), where R is the group of the formula (II), in which R.sub.1 is aryl and alkylaryl group, and n is 0 and 1.
According to this invention by condensation of N-substituted derivatives of N-methyl-3-phenyl-3-hydroxypropylamine (XV), where R.sub.1 is benzyl and p-nitrobenzyl group and n is 0, and p-trifluoromethylchlorbenzene (XVI) prepared N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine (I), where R is the group of the formula (II), in which n and R are the same as in the compound (XV), which by the reaction with chloroformic acid esther (XVII), where R.sub.1 aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, are converted to N-substituted derivatives of N-methyl-3-(p -trifluoromethylphenoxy)-3-phenylpropylamine (I), where R is the group of the formula (II), in which R.sub.1 is the same as in the compound (XVII), and n is 1, from which is prepared the compound of the formula (I), in which R is hydrogen (Fluoxetin), by basic hydrolysis and/or catalytic hydrogenolysis, when R is the group of the formula (II), in which R.sub.1 is benzyl and p-nitrobenzyl group, and n is 0 and 1.

REFERENCES:
Robertson, et al., "Synthesis of 14C- and 3H-Labaled Fluoxetine, A Selective Serotonin Uptake Inhibitor", Journal of Labelled Compounds and Radiopharmaceuticals, vol. XXIV, No. 11, (1987) pp. 1397-1404.
Cooley, et al., Amine Dealkylations with Acyl Chlorides, Synthesis No. 1, (1989) pp. 1-7.
Abstract of 89-1015, 03 Mar. 1989, Kairisalo et al., CA 114: 42266.

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