4-[-(Alkoxy or polyhaloalkoxy)-benzamido]cyclohexanones

Details 4-[-(Alkoxy or polyhaloalkoxy)-benzamido]cyclohexanones 4-[-(Alkoxy or polyhaloalkoxy)-benzamido]cyclohexanones

1975-02-24

1976-06-01

Hines, Robert V.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603407, 260563R, 2605709, 424278, C07C10326

Patent

active

039609456

ABSTRACT:
3-R-3-(Ac.sub.2 NH)-9-R'-9-(Ac.sub.1 NH)-1,5-dioxaspiro[5.5]undecane (I), where R and R' are each hydrogen or lower-alkyl, Ac.sub.1 is lower-alkanoyl or 4-Q.sub.1 -benzoyl and Ac.sub.2 is 4-Q.sub.2 -benzoyl where Q.sub.1 and Q.sub.2 each is lower-alkoxy or polyhalo-lower-alkoxy, are antifertility agents. The compounds are prepared by di-acylating 3-R-9-R'-1,5-dioxaspiro[5.5]undecan-3,9-diamine (II) or mono-acylating 9-(Ac.sub.1 NH)-3-R-9-R'-1,5-dioxaspiro[5.5]undecan-3-amine (IV). IV and II are prepared by oxidizing 4-(Ac.sub.1 NH)-4-R'-cyclohexanol (VI) to produce 4-(Ac.sub.1 NH)-4-R'-cyclohexanone (VII), reacting VII with 2-NO.sub.2 -2-R-1,3-propanediol to produce 3-R-3-NO.sub.2 -9-(Ac.sub.1 NH)-9-R'-1,5-dioxaspiro[5.5]undecane (VIII), reducing VIII to produce the corresponding 3-amine (IV) and hydrolyzing IV to the corresponding 3,9-diamine (II). Methods of preparing VI are shown.

REFERENCES:
patent: 3352884 (1967-11-01), Fonken et al.
patent: 3840598 (1974-10-01), Lesher
patent: 3869443 (1975-03-01), Lesher
bretschneider et al., Monetsh. Chem. 1972, 103(5), pp. 1380-1382.

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