ChemicalBook CAS DataBase List 1-CYANOACETYLPIPERIDINE

1-CYANOACETYLPIPERIDINE synthesis

6synthesis methods

Product Name:1-CYANOACETYLPIPERIDINE
CAS Number:15029-30-8
Molecular formula:C8H12N2O
Molecular Weight:152.19

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Yield: 92%

Reaction Conditions:

in neat (no solvent) at 20;Inert atmosphere;

Steps:

Preparation of N-substituted cyanacetamides 1 and 4 - precursors to the cyanoximes
Neat ethylcyanoacetate reacts at room temperature with neat secondary amines at solvent-free conditions to form respective amides [44,45]. The general procedure involves mixing neat piperidine or morpholine with NC-CH₂-C(O)OC₂H₅ at 1.5:1 ratio under stirring and an N₂ blanket. These reactions within 24-60h at room temperature lead to prePiPCO (1) and preMCO (4) in high yields (Scheme 1). Course of both reactions was monitored by TLC watching disappearance of the cyanoacetylacetate. Since starting compounds and final cyan-acetamides do not contain chromophores, an I₂-chamber was used for plates’ development. Thus, thick off-white precipitates of 1 and 4 were filtered under vacuum, washed with small portions (～20mL) of toluene and hexane (～25mL), and then dried in a vacuum dessicator charged with concentrated H₂SO₄ for several days until smell of the amine was no longer detectable. Data for 1: yield 92%, m.p. 87-90°C. The ring methylene protons in both precursors and target cyanoximes demonstrate complex non-first order ¹H NMR spectra of AA′BB′ spin systems. The ¹H NMR, ppm, in dmso-d₆: 4.01 (singlet, 2H), ring protons - 3.41 (“triplet”, 2H), 3.28 (“tiplet”, 2H), 1.53 (multiplet, 6H). Mass-spectrometry, positive FAB (Ar): for C₈H₁₂N₂O, calculated - 152.12 (found - 152.1). Data for 4: yield ～100%, m.p. 78-81°C, R_f=0.12 in EtOAc/hexane (1:2) mobile phase. The ¹H NMR, ppm, in dmso-d₆: 4.03 (singet, 2H), ring protons - 3.56 (“quartet”, 4H - next to O), 3.43 (“triplet”, next to N), 3.34 (“triplet”, next to N). Mass-spectrometry, positive FAB (Ar): for C₇H₁₀N₂O₂, calculated - 154.07 (found - 154.08).

References:

Riddles, Courtney N.;Whited, Mark;Lotlikar, Shalaka R.;Still, Korey;Patrauchan, Marianna;Silchenko, Svitlana;Gerasimchuk, Nikolay [Inorganica Chimica Acta,2014,vol. 412,p. 94 - 103]

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