1,3-Dimethyl-2,6-diphenyl­piperidin-4-one

P Nithya; Venkatesha R Hathwar; T Maiyalagan; Canan Kazak; F Nawaz Khan

doi:10.1107/S1600536809003419

. 2009 Jan 31;65(Pt 2):o439. doi: 10.1107/S1600536809003419

1,3-Dimethyl-2,6-diphenylpiperidin-4-one

P Nithya ^a, Venkatesha R Hathwar ^b, T Maiyalagan ^a, Canan Kazak ^c, F Nawaz Khan ^a,^*

PMCID: PMC2968156 PMID: 21582024

Abstract

In the title moleclue, C₁₉H₂₁NO, the 4-piperidone ring adopts a chair conformation in which the two benzene rings and the methyl group attached to C atoms all have equatorial orientations. In the crystal structure, centrosymmetric dimers are formed through weak intermolecular C—H⋯O hydrogen bonds [the dihedral angle between the aromatic rings is 58.51 (5)°].

Related literature

For general background, see: Badorrey et al. (1999 ▶); Grishina et al. (1994 ▶); Nalanishi et al. (1974 ▶); Perumal et al. (2001 ▶); Ponnuswamy et al. (2002 ▶). For a related crystal structure, see: Gayathri et al. (2008 ▶). For the synthetis, see: Noller & Baliah (1948 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶, 1995 ▶).

Experimental

Crystal data

C₁₉H₂₁NO
M _r = 279.37
Triclinic,
a = 5.9201 (2) Å
b = 10.9749 (3) Å
c = 12.8247 (3) Å
α = 80.2961 (12)°
β = 86.673 (2)°
γ = 76.4499 (11)°
V = 798.30 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 (2) K
0.28 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.943, T _max = 0.987
12316 measured reflections
3143 independent reflections
2446 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.116
S = 1.02
3143 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003419/lh2761sup1.cif

e-65-0o439-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003419/lh2761Isup2.hkl

e-65-0o439-Isup2.hkl^{(151KB, 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
C1—H1⋯O1ⁱ	0.98	2.56	3.3535 (16)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at the IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

The synthesis of 4-piperidones is of current interest due to their potential medical applications (Grishina et al., 1994, Ponnuswamy et al., 2002). 4-Piperidones have been found to exhibit blood cholesterol-lowering activities (Nalanishi et al., 1974). Various piperidones and piperidine derivatives are present in numerous alkaloids (Badorrey et al., 1999). Piperidones are also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al., 2001).

In the title molecule, C₁₉H₂₀NO (Fig. 1), the piperidine ring adopts a chair conformation (Cremer & Pople, 1975; Nardelli, 1995). The phenyl rings at positions 2 and 6 and the methyl group attached at position 3 all have equatorial orientations. In the related crystal structure of r-2,c-6-Bis(4-chlorophenyl)-t-3-isopropyl-1-nitrosopiperidin-4-one, the piperidine ring also adopts a chair conformation (Gayathri et al., 2008) but the three substituents on the C atoms of the ring are in axial orientations. In the crystal structure, centrosymmetric dimers are formed through weak intermolecular C—H···O hydrogen bonds (Fig. 2).

Experimental

The sythesis was based on a procedure in the literature (Noller & Baliah, 1948). Benzaldehyde (0.20 mol), 3-methyl-2-butanone (0.10 mol) and ammonium acetate (0.10 mol) were dissolved in 80 ml of distilled ethanol and heated over a boiling water bath, with shaking until a yellow colour developed and ultimately changed to orange. The solution was left undisturbed for 14 h. The precipitated solid was filtered and purified by recrystallization from ethanol. The piperidone intermediate was then dissolved in acetone and was alkyalted with methyliodide in the presence of potassium carbonate.