Process for the preparation of fluoxetine

Details Process for the preparation of fluoxetine Process for the preparation of fluoxetine

1990-11-23

1992-11-24

Cintins, Marianne M.

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

Organic compounds

Amino nitrogen containing

564342, 564346, C07C21306

Patent

active

051664372

ABSTRACT:
An improved process for the preparation of fluoxetine. The invention is concerned with an improved process for the preparation of the antidepressant, fluoxetine hydrochloride, or N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride, by simultaneous debenzylation and catalytic hydrogenation of 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base with the aid of Pd/C, Pt/C or Pd-Pt/C at a hydrogen pressure of 5 bar at 50.degree. C. with ethyl acetate as a solvent to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol. This compound is then selectively etherified with 1-chloro-4-trifluoromethylbenzene in N-methylpyrrolidone at 80.degree. C. in the presence of potassium t-butoxide to form N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine, or fluoxetine base, which is transformed in a known manner to fluoxetine hydrochloride, or N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine hydrochloride. The yield of fluoxetine hydrochloride is 85-87% of the theoretical.

REFERENCES:
patent: 3151124 (1964-09-01), Huebner
patent: 3642896 (1972-02-01), Collin
patent: 4296126 (1981-10-01), Nedelec et al.
patent: 4314081 (1982-02-01), Molloy et al.
patent: 4500541 (1985-02-01), Hausberg et al.
Carey, Organic Chemistry pp. 608-609.
Fieser et al., "Reports for Organic Synthesis", vol. 1 pp. 1109-1110 (1967).
Danheisen et al. "Reports for Organic Synthesis", vol. 9, p. 381 (1981).
"Synthesis of .sup.14 C- and .sup.3 H- Labeled Fluoxetine, A Selective Serotonin Uptake Inhibitor", Journal of Labelled Compounds and Radiopharmaceuticals, by David W. Robertson et al., vol. 24, No. 11, 1987, John Wiley & Sons, Ltd., pp. 1397 to 1404.
The Search Report from European Application No. 90104018.8, filed Mar. 1, 1990.
"Reagents for Organic Synthesis", Fieser et al., vol. 1, pp. 1109-1110, 1967.
"Reagents for Organic Synthesis", Danheiser et al., vol. 9, p. 381, 1981.
Patent Abstracts of Japan, vol. 10, No. 239 (C-367) (2295), Aug. 19, 1986, concerning JP-A-6172736 (Toyo Soda Mfg. Ltd.), Apr. 14, 1986.
Asymmetric Synthesis of Both Enantiomers of Tomoxetine and Fluoxetine. Selective Reduction of 2,3-Epoxycinnamyl Alcohol with Red-Al, by Y. Gao and K. B. Sharpless, J. Org. Chem., vol. 53, pp. 4081-4084 (1988).

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