Thies, Heinrich and Schönenberger, Helmut and Qasba, P. K. (1969) Reactions of alpha -aminonitriles. IV. Dimerization of alpha -piperidinoacetonitrile with tert-butylmagnesium chloride. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 302 (3), pp. 161-168.
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alpha -Piperi-dinoacetonitrile (I) (0.2 mole) in 200 ml. Et2O was treated with 0.4 mole tert-BuMgCl in 500 ml. Et2O with cooling 2 hrs. to give 70% 3-amino-2,4-dipiperidinocrotononitrile (II), m. 86-7 Deg. With half the above amts. of reagents, II was obtained in 90% yield, and 0.054 mole isobutane was collected. The isobutane was identified by gas chromatog. in 30% benzyl ether on C22 firebrick with H as carrier gas at 40 Deg. The ir spectrum of II is reported and the mechanism of II formation is discussed. I was also treated with tert-BuONa in PhMe to give 19.4% II.
|Additional information (public):||CAN 71:61151 27 Heterocyclic Compounds (One Hetero Atom) 677-22-5 Role: RCT (Reactant), RACT (Reactant or reagent) (dimerization of piperidineacetonitrile by); 3010-03-5 Role: RCT (Reactant), RACT (Reactant or reagent) (dimerization of, with tert-butylmagnesium chloride); 21901-98-4P; 23056-58-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Dimerization (of piperidineacetonitrile with tert-butylmagnesium chloride) nitriles aminodipiperidinocrotono crotononitriles amino piperidino piperidinocrotononitriles amino|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 06:20|
|Last Modified:||19 Nov 2010 06:20|