Method for preparation of aryl substituted alefinic secondary am

Details Method for preparation of aryl substituted alefinic secondary am Method for preparation of aryl substituted alefinic secondary am

1996-04-23

1997-09-02

Owens, Amelia

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546314, 546315, 546329, C07D21362

Patent

active

056633564

ABSTRACT:
Patients susceptible to or suffering from central nervous system are treated by administering an effective amount of an aryl substituted olefinic amine compound, such as (E)-metanicotine. (E)-metanicotine is provided from nicotine. Nicotine is reacted with ethyl chloroformate to produce ethyl N-methyl-N-[4-chloro-4-(3-pyridyl)butyl]carbamate, which then is reacted in the presence of potassium tert-butoxide, tetrahydrofuran and dimethylformamide to produce (E)-metanicotine N-ethyl carbamate, which then is subjected to hydrolysis using hydrochloric acid to produce a reaction mixture containing (E)-metanicotine. The reaction mixture containing (E)-metanicotine is adjusted to a slightly basic pH, and then contacted with dichloromethane. The resulting water immiscible phase then is separated from the aqueous phase. The aqueous phase, then is adjusted to a very basic pH, and then contacted with methyl tert-butyl ether. (E)-metanicotine is taken up by the methyl tert-butyl ether, and after separation of the methyl tert-butyl ether from the aqueous phase, the desired product is separated from the methyl tert-butyl ether.

REFERENCES:
patent: 5212188 (1993-05-01), Caldwell et al.
LaForge, F. B., "The Preparation and Properties of Some New Derivatives of Pyridine", J. Am. Chem. Soc., vol. 50, pp. 2477-2483 (1928).
Acheson, R. M. et al., "Transformations involving the Pyrrolidine Ring of Nictone", J. Chem. Soc., Perking Trans. 1., vol. 2, pp. 579-585 (1980).
Loffler et al., Chem. Ber., vol. 42, pp. 3431-3438 (1909).
Joyce, N. J. et al., "The Formation of 1-Methyl-3-Nicotinoylpyrrolidine from Nicotine-1'-Oxide", Heterocycles, vol. 29, No. 7, pp. 1335-1342 (1989).
Frank, W. C. et al., "Palladium-Catalyzed Vinylic Substitution Reactions with Heterocyclic Bromides", J. Org. Chem., vol. 43, No. 15, pp. 2947-2949 (1978).
Malek, N. J. et al., "Palladium-Catalyzed Synthesis of Cinnamylamines", J. Org. Chem . . . , vol. 47, pp. 5395-5397 (1982).
Sprouse, C. T. et al., "Isomers of metanicotine and the Pinner-Etard reaction", In Abstracts of Papers, Coresta/TCRC, pp. 32-33 (1972).
Cooper, Donald A. et al., "Femtogram On-column Detection of Nicotine by Isotope Dilution Gas Chromatography/Negative Ion Detection Mass Spectrometry", Biological Mass Spectrometry, vol. 22, (1993).
Pinner, A., "Ueber Nicotin (Metanicotin)", Chem. Ber., pp. 1053-1061 (1894).
Pinner, A., "Ueber Nicotin", Chem. Ber., pp. 2861-2870 (1894).

Affiliated with

Also associated with

Rating

Method for preparation of aryl substituted alefinic secondary am does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for preparation of aryl substituted alefinic secondary am, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for preparation of aryl substituted alefinic secondary am will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-309810