1-Acetyl-t-3-ethyl-r-2,c-6-bis­(4-methoxy­phen­yl)piperidin-4-one

K Ravichandran; S Ponnuswamy; R Rajesh; V Mohanraj; M N Ponnuswamy

doi:10.1107/S1600536809054737

. 2010 Jan 9;66(Pt 2):o275. doi: 10.1107/S1600536809054737

1-Acetyl-t-3-ethyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one

K Ravichandran ^a, S Ponnuswamy ^b, R Rajesh ^b, V Mohanraj ^b, M N Ponnuswamy ^a,^*

PMCID: PMC2979765 PMID: 21579712

Abstract

In the title compound, C₂₃H₂₇NO₄, the piperidine ring adopts a distorted boat conformation. The methoxy groups lie in the plane of benzene rings to which they are attached [maximum deviations of 0.014 (3) and 0.007 (3) Å]. The benzene rings are oriented at angles of 67.2 (1) and 87.0 (1)° with respect to the best plane through the four co-planar atoms of the piperidine ring.

Related literature

For general background to piperidine derivatives, see: Aridoss et al. (2008 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₃H₂₇NO₄
M _r = 381.46
Orthorhombic,
a = 8.6736 (11) Å
b = 13.4578 (16) Å
c = 17.547 (2) Å
V = 2048.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.979, T _max = 0.983
11102 measured reflections
2646 independent reflections
1926 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.138
S = 1.08
2646 reflections
257 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.19 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054737/bt5144sup1.cif

e-66-0o275-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054737/bt5144Isup2.hkl

e-66-0o275-Isup2.hkl^{(127.3KB, hkl)}

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

Acknowledgments

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar’s College, Velur, Namakkal, TN, India, for the encouragement to pursue the programme.

supplementary crystallographic information

Comment

Piperidine derivatives are the valued heterocyclic compounds in the field of medicinal chemistry. The compounds possessing an amide bond linkage have a wide range of biological activities such as antimicrobial, antinflammatory, antiviral, antimalarial and general anaesthetics. Furtheremore, the amides derived from chloroacetylchloride also gain significant importance in medicinal field as evidenced by their varied pharmacological activities (Aridoss et al., 2008). The crystallographic study of the title compound has been carried out to establish the molecular structur

The ORTEP diagram of the title compound is shown in Fig. 1. The piperidine ring in the molecule adopts a distorted boat conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q₂ = 0.636 (3) Å, q₃ = 0.089 (3) Å, φ₂ = 286.2 (2)° and Δ_s(C3 & C6)= 15.4 (3)°. The methoxy groups lie in the plane of phenyl rings and the phenyl rings are oriented at angles of 67.2 (1)° and 87.0(1°) with the best plane of piperidine ring. The sum of the bond angles around the atom N1(358.5°) of the piperidine ring in the molecule is in accordance with sp² hybridization. The crystal structure is stabilized by intramolecular C—H···O interactions.

Experimental

To a solution of t-3-ethyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one (3.39 g) in anhydrous benzene (60 ml) was added triethylamine (2.78) and acetylchloride (1.42 ml). The contents were allowed to reflux on a water bath for 12 h. The precipitated ammonium salt was filtered off and the filterate was washed with water. The organic layer was dried over anhydrous Na₂SO₄, concentrated and crystallized from benzene:pet-ether (60–80°C) in the ratio of 9:1.