Arylperfluoroalkanes

Details Arylperfluoroalkanes Arylperfluoroalkanes

1976-02-20

1978-01-31

Love, Ethel G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260649DP, 424330, C07C 2500

Patent

active

040715701

ABSTRACT:
New fluoro derivatives of aralkylamine compounds, particularly 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine, as well as the N-alkyl and the N,N-dialkyl derivatives thereof are prepared by reaction of 2-bromobenzonitrile with benzylmagnesium chloride to produce 2'-bromo-2-phenylacetophenone; oxidation of said acetophenone with selenous acid to produce 2-bromobenzil; conversion of the benzil compound by treatment with sulfur tetrafluoride to the corresponding 2-bromo-.alpha.,.alpha.-.alpha.',.alpha.'-tetrafluorobibenzyl;followed by reaction of the 2-bromobibenzyl compound with a metal cyanide to produce the corresponding 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzonitrile. This nitrile compound is then reduced with lithium aluminum hydride to produce the corresponding benzylamine, which is then converted, if desired, to the N-alkyl and/or N,N-dialkyl 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine. Alternatively, the nitrile or the precursor bromobibenzyl can be converted by Grignard reactions to the corresponding .alpha.-alkyl or .alpha.,.alpha.-dialkylbenzylamine which can then be converted if desired to the corresponding N-alkyl and/or N,N-dialkyl substituted benzylamine compound. The phenyltetrafluoroethylbenzylamine as well as its N-alkyl and N,N-dialkyl derivatives are active as antiarrhythmic agents.

REFERENCES:
patent: 3297591 (1967-01-01), Chow
Malichenko et al., "Chem. Abstracts", vol. 61, p. 1779c (1964).
Yagupol'skii et al., "Chem. Abstracts", vol. 63, p. 17937c (1965).

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