Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-05-16
1976-08-31
Curtis, Allen B.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2605708R, 2605709, C07C 8728
Patent
active
039781275
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.
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patent: 3226448 (1965-12-01), Gordon et al.
Yagupol'skii et al., "Tetrafluorobibenzyl Derivatives", in J. Gen. Chem. USSR 35: 1616-1623, 9/1965.
Tomita et al., "Synthesis of Ammonium Comp'ds", in J. Pharm. Society vol. 73, pp. 760-765.
Christy Marcia E.
Engelhardt Edward L.
Behan J. Jerome
Curtis Allen B.
Merck & Co. , Inc.
Szura Daniel T.
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