1-(pyridin-2-yl)-N-[(1R,2R)-2-{[(pyridin-2-yl)methylidene]amino}cyclohexyl]methanimine synthesis
- Product Name:1-(pyridin-2-yl)-N-[(1R,2R)-2-{[(pyridin-2-yl)methylidene]amino}cyclohexyl]methanimine
- CAS Number:284497-48-9
- Molecular formula:C18H22N4
- Molecular Weight:294.3941
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Yield:284497-48-9 78%
Reaction Conditions:
in methanol;Reflux;
Steps:
N,N'-(1R,2R)-Cyclohexane-1,2-diylbis[1-(pyridine-2-yl)methanimine] (2a)
General procedure: A solution of 4.4 mmol (0.5 g) of (R,R)-1,2-cyclohexanediimine 1 {[α]D -8.17°C (c 8.7, C6H6)} in 30 mL of methanol was boiled for 30 min, then a solution of 9 mmol (0.96 g) of 2-pyridine-carboxaldehyde in 20 mL of methanol was added dropwise. The mixture was stirred for 4 h and left overnight. The reaction was monitored by the TLC method up to the complete aldehyde conversion. A white precipitate was filtered off, washed with hexane, and dried. Yield 78% (0.91 g) [α] D23 264 (c 1.0,MeOH), mp 126-127°C, (mp 128-129°C [34]). IRspectrum, (KBr), ν, cm-1: 1645 m (C=N). 1 NMRspectrum (CDCl3), δ, ppm: 1.45-1.52 m (2H, C3,6HAHB),1.79-1.87 m (2H, C3,6HAHB, 4H C4,5HAHB), 3.43-3.58m (2H, NC1,2H) 7.18 d.d. (2H, C11,11’H, 3JHH = 7.5,4.8 Hz), 7.60 d.d (2H, C10,10'H, 3J = 7.5, 1.5 Hz), 7.85br.d (2H, CH9,9'H, 3J = 7.5 Hz), 8.28 s (2H, CH=N),8.51 d (2H, C12,12'H). 1 NMR spectrum (CD3OD), δ,ppm: 1.50-1.62 m (2H, C3,6HAHB), 1.81-1.91 m (2H,C3,6HAHB; 4H C4,5HAHBH), 3.49-3.58 m (2H, NC1,2H),7.37 d (2H, C11,11'H, 3J = 5.5 Hz), 7.80 d.d (2H,C10,10'H, 3J = 7.8, 1.2 Hz), 7.90 d (2H, C12,12'H, J =5.5 Hz). 13C NMR spectrum (CD3OD), δC, ppm: 24.7(C4,5), 32.9 (C3,6), 74.0 (C1,2), 121.6 (C9,9'), 125.5(C11,11'), 137.3 (C10,10'), 149.0 (C12,12'), 154.7 (N=CH),161.4 (C8,8'). Found, %: C 73.91; H 6.81; N 19.10.C26H24N4. Calculated, %: C 73.97; H 6.85; N 19.18.
References:
Nindakova;Badyrova;Sadykov, E. Kh.;Ushakov;Vanzarakshaeva, S. Ch. [Russian Journal of General Chemistry,2017,vol. 87,# 11,p. 2537 - 2545][Zh. Obshch. Khim.,2017,vol. 87,# 11,p. 1794 - 1803,15]
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$10.60/10gm:
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$20.00/25g
284497-48-9
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inquiry