[(4E)-3-Ethyl-1-methyl-2,6-di­phenyl­piperidin-4-yl­idene]amino 3-methyl­benzoate

T Vinuchakkaravarthy; R Sivakumar; T Srinivasan; V Thanikachalam; D Velmurugan

doi:10.1107/S1600536813024276

. 2013 Sep 18;69(Pt 10):o1545. doi: 10.1107/S1600536813024276

[(4E)-3-Ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene]amino 3-methylbenzoate

T Vinuchakkaravarthy ^a, R Sivakumar ^b, T Srinivasan ^a, V Thanikachalam ^b, D Velmurugan ^a,^*

PMCID: PMC3790411 PMID: 24098230

Abstract

In the title compound, C₂₈H₃₀N₂O₂, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl rings and methyl group substituted on the heterocycle. In the crystal, C—H⋯π interactions result in chains of molecules running parallel to the a-axis direction.

Related literature

For the synthesis and background to the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009 ▶, 2011 ▶). For crystal structures of related compounds, see: Park et al. (2012a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₈H₃₀N₂O₂
M _r = 426.54
Triclinic,
a = 10.5220 (15) Å
b = 11.8295 (16) Å
c = 11.987 (3) Å
α = 112.871 (11)°
β = 97.939 (11)°
γ = 110.123 (8)°
V = 1225.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.986, T _max = 0.986
18615 measured reflections
5042 independent reflections
3610 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.139
S = 1.03
5042 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813024276/pv2635sup1.cif

e-69-o1545-sup1.cif^{(31.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024276/pv2635Isup2.hkl

e-69-o1545-Isup2.hkl^{(241.9KB, hkl)}

Click here for additional data file.^{(9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813024276/pv2635Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.93	2.93	3.761 (2)	149
C23—H23⋯Cg1ⁱⁱ	0.93	2.89	3.730 (3)	151

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection·TV, TS and DV thank the UGC (SAP–CAS) for providing facilities to the department.

supplementary crystallographic information

1. Comment

Piperdin-4-one nucleus is an important pharmacophore due to its broad spectrum of biological actions ranging from antibacterial to anticancer (Parthiban et al., 2009; 2011). Hence, the synthesis and steriochemical analysis of piperdin-4-one nucleus based pharmacophores has gained much interest in the field of medicinal chemistry.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Park et al., 2012a; 2012b). The piperidone ring (N1/C1—/C5) adopts a chair conformation with puckering parameters: Q =0.570 (2) Å, θ = 177.6 (2)° and φ = 3439 (4)° (Cremer & Pople, 1975).

In the crystal, the molecules are stabilized by intermolecular C11—H11···Cg1ⁱ and C23—H23···Cg1ⁱⁱ hydrogen bond interactions, where Cg1 is the center of gravity of ring atoms involving C15—C20 of the interacting molecules, respectively (Table 1). The packing of the molecules within the crystal is shown in Fig. 2.

2. Experimental

3-Ethyl-2,6-diphenylpiperidin-4-one was synthesized by Mannich condensation using benzaldehyde (2 mol), ammonium acetate (1 mol) and ethyl methyl ketone (1 mol) in absolute ethanol and warmed for 30 min and stirred overnight at room temperature. The product was treated with methyl iodide (1.5 mol) in the presence of potassium carbonate (2 mol) in acetone (10 ml) and refluxed to give 1-methyl-3-ethyl-2,6-diphenylpiperidin-4-one. The oximation was done by hydroxylamine hydrochloride (2 mol) in presence of sodium acetate (2 mol) in ethanol (10 ml) and refluxed. The resulting oxime (0.5 g, 1.55 mmol) was stirred with dry pyridine (5 ml), added 3-methylbenzoic acid (0.23 g, 1.7 mmol) followed by phosphorus oxychloride (0.21 ml, 2.3 mmol) in dropwise addition and stirred at ambient temperature for 15 min; the progress of the reaction was monitored by thin layer chromatography. Upon completion of the reaction, saturated sodium bicarbonate solution (8 ml) was added to the reaction mixture, solid was formed and it was filtered and dried to get a white solid (0.58 g, 87.8%) which was recrystallized from ethanol to yield crystals suitable for X-ray crystallographic studies.