Ethyl 4-[2-(3,5-dimethyl-4-oxo-2,6-diphenyl­piperidin-1-yl)-2-oxoeth­yl]piperazine-1-carboxyl­ate

Mannangatty Rani; Rajamanickam Ramachandran; Senthamaraikannan Kabilan; Yeon Tae Jeong

doi:10.1107/S1600536811003412

. 2011 Feb 2;67(Pt 3):o541. doi: 10.1107/S1600536811003412

Ethyl 4-[2-(3,5-dimethyl-4-oxo-2,6-diphenylpiperidin-1-yl)-2-oxoethyl]piperazine-1-carboxylate

Mannangatty Rani ^a, Rajamanickam Ramachandran ^b, Senthamaraikannan Kabilan ^a, Yeon Tae Jeong ^b,^*

PMCID: PMC3052019 PMID: 21522309

Abstract

In the title compound, C₂₈H₃₅N₃O₄, the piperidine ring adopts a boat conformation while the piperazine ring adopts a chair conformation with an equatorial orientation of the phenyl groups. The dihedral angle between the mean planes of the benzene rings is 74.14 (8)°. The molecular conformation is stabilized by a weak intramolecular C—H⋯N interaction and the crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity of related structures, see: El-subbagh et al. (2000 ▶); Emami et al. (2006 ▶); Foroumadi et al. (2007 ▶); Katritzky & Fan (1990 ▶); Mobio et al. (1989 ▶). For geometrical analysis, see: Cremer & Pople (1975 ▶); Emami et al. (2006 ▶); Foroumadi et al. (2007 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₈H₃₅N₃O₄
M _r = 477.59
Monoclinic,
a = 10.9073 (3) Å
b = 19.1940 (6) Å
c = 12.2246 (3) Å
β = 91.809 (2)°
V = 2558.00 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.975, T _max = 0.984
31692 measured reflections
6941 independent reflections
4703 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.142
S = 1.01
6941 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003412/zq2086sup1.cif

e-67-0o541-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003412/zq2086Isup2.hkl

e-67-0o541-Isup2.hkl^{(339.7KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2	0.98	2.51	3.1788 (17)	125
C8—H8⋯O2ⁱ	0.93	2.54	3.4406 (19)	162
C24—H24A⋯O1ⁱⁱ	0.97	2.56	3.520 (2)	169

Open in a new tab

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

Acknowledgments

This study was supported financially by Pukyong National University in the 2010 post-doc programme. The authors are thankful to the SAIF, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

Several interesting investigations have been carried out with piperidine based heterocyclic compounds and these compounds were found to exhibit numerous pharmacological properties and biological activities such as anticancer, antimicrobial, anti-inflammatory, antiviral, antimalarial and anesthetics (El-subbagh et al., 2000; Mobio et al., 1989; Katritzky & Fan, 1990). Similarly, some compounds containing piperazine are used as antibiotic drugs, e.g., Norfloxacin, Ciprofloxacin, Enoxacin, Ofloxacin and Levofloxacine (Emami et al., 2006; Foroumadi et al., 2007).

In the title compound, C₂₈H₃₅N₃O₄, the piperidine ring adopts a boat conformation. The corresponding puckering parameters (Cremer & Pople, 1975) and smallest displacement asymmetry parameters (Nardelli, 1983) are q₁ = 0.6111 (15) Å, q₂ = -0.0839 (15) Å, Q_T= 0.6168 (15) Å, and θ = 97.81 (14) °. Unlike, the piperazine ring adopts a chair conformation with q₁ = 0.0367 (15), q₂ = 0.5606 (15) Å, Q_T= 0.5618 (15) Å and θ = 3.75 (15)°. The phenyl groups are orientated to the same side of the piperazine ring. The dihedral angle between the mean planes of the benzene rings is 74.14 (8)°. The molecular conformation is stabilized by a weak intramolecular C5-H5···N2 interaction and the crystal packing by the weak intermolecular C8-H8···O2ⁱ and C24-H24···O1ⁱⁱ interactions [Table 1; symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z].

Experimental

A mixture of N-chloroacetyl-3,5-dimethyl-2,6-diphenylpiperidin-4-one (0.005 mol), triethylamine (0.01 mol) and N-ethoxycarbonylpiperazine (0.005 mol) in toluene were refluxed for about 6–8 h. After the completion of reaction, excess of solvent was removed under reduced pressure. The obtained residue was column chromatographed on silica gel using benzene:ethyl acetate (2:1) mixture as an eluent which afforded the title compound in good yield. Colourless crystals were grown by slow evaporation method using ethanol as solvent.