Thies, Heinrich and Schönenberger, Helmut and Qasba, P. K. (1969) Reactions of alpha -aminonitriles. V. Adduct formation and dimerization of alpha -piperidinoacetonitrile in reaction with butylmagnesium chloride. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 302 (3), pp. 168-174.
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alpha -Piperidinoacetonitrile (I) was treated with BuMgCl in the ratio 2:1-1:2 and allowed to react for 20 min. or 2 hrs. to give 28-43% 3-amino-2,4-dipiperidinocrotononitrile (II). The yield of II was affected more by the ratio of the reagents than by the reaction time. The other product was 1-piperidino-2-hexanone (III), b15 120 Deg. The formation of II proceeds by addn. of BuMgCl to I, addn. of a second mol. of I, followed by a second mol. of BuMgCl and hydrolysis of the complex to give II, C4H10, and Mg(OH)Cl. A similar addn. of 2 mols. BuMgCl to I is proposed for the formation of III.
|Additional information (public):||CAN 71:38743 27 Heterocyclic Compounds (One Hetero Atom) 21901-95-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 3010-03-5 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with butylchloromagnesium); 693-04-9 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with piperidinoacetonitrile)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Nitriles Role: RCT (Reactant), RACT (Reactant or reagent) (amino) piperidinoacetonitrile Grignard adduct adduct Grignard piperidinoacetonitrile Grignard adduct piperidinoacetonitrile Dimerization piperidinoacetonitrile amino dipiperidinocrotonitrile dipiperidinocrotonitrile 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 06:18|
|Last Modified:||19 Nov 2010 06:18|