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Reduction of alpha -amino nitriles with metallic sodium in toluene

Thies, Heinrich and Schönenberger, Helmut and Qasba, P. K. (1965) Reduction of alpha -amino nitriles with metallic sodium in toluene. Tetrahedron letters (3), pp. 163-166.

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Abstract

RR1C(CN)- NR2R3 (R = Me or Ph, R1 = H or Me, R2 and R3 = Et or R2R,3 = piperidino), treated with Na in refluxing MePh gave, in addn. to the corresponding RR1CHNR2R3, ethylenediamine derivs., [RR1C(NR2R3)]2, which were formed by the replacement of 1 CN group by the CN-free residue of another mol. alpha -Piperidinoisobutyronitrile, m. 43-5 Deg (0.75 mole), in 250 cc. MePh added slowly to 0.75 g.-atom powd. Na in hot MePh gave 42% N-isopropylpiperidine, b15 42 Deg, and 8% 2,3-dipiperidino-2,3-dimethylbutane, b0.4 110-13 Deg. alpha -Piperidinopropionitrile, b15 92-5 Deg, gave similarly 43% 1-ethylpiperidine, b20 40 Deg, and 22% 2,3-dipiperidinobutane, b15 148-9 Deg. PhCH(CN)NEt2, b13 134-5 Deg, yielded 39% PhCH2NEt2, b16 85-7 Deg, and 45% reddish yellow [PhCH(NEt2)]2, b0.4 140 Deg.

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Article

Additional information (public):

CAN 62:51519 37 Heterocyclic Compounds (One Hetero Atom) 30680-88-7 (Derived from data in the 7th Collective Formula Index (1962-1966); 5097-99-4; 62842-38-0 Role: PRP (Properties), RCT (Reactant), RACT (Reactant or reagent) (Reduction of alpha -amino nitriles with metallic sodium in toluene); 766-09-6P; 2273-41-8P Role: SPN (Synthetic preparation), PRP (Properties), PREP (Preparation) (Reduction of alpha -amino nitriles with metallic sodium in toluene); 69010-98-6 (Piperidine, tetramethyl-) (derivs.); 18860-15-6 (Toluene, ion (-1) (nitrile redn. in presence of); 766-79-0P (Piperidine, 1-isopropyl-); 772-54-3P (Benzylamine, N,N-diethyl-); 782-07-0P (Piperidine, 1,1'-(1,2-dimethylethylene)di-); 785-94-4P (Piperidine, 1,1'-(tetramethylethylene)di-); 800-13-5P (Ethylenediamine, N,N,N',N'-tetraethyl-1,2-diphenyl-) Role: PREP (Preparation) (prepn. of); 7440-23-5 (Sodium) (alpha -amino nitrile redn. by)

Institutions:

Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger

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