2-Chloro-1-(3,3-dimethyl-2,6-di­phenyl­piperidin-1-yl)ethanone

K Prathebha; B K Revathi; G Usha; S Ponnuswamy; S Abdul Basheer

doi:10.1107/S1600536813022289

. 2013 Aug 14;69(Pt 9):o1424. doi: 10.1107/S1600536813022289

2-Chloro-1-(3,3-dimethyl-2,6-diphenylpiperidin-1-yl)ethanone

K Prathebha ^a, B K Revathi ^a, G Usha ^a,^*, S Ponnuswamy ^b, S Abdul Basheer ^b

PMCID: PMC3884441 PMID: 24427057

Abstract

In the title compound, C₂₁H₂₄ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7 (1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64 (10) and 70.8 (1)°. The molecular structure features short intramolecular C—H⋯Cl and C—H⋯O contacts. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the synthesis of the title compound, see: Venkatraj et al. (2008 ▶). For the biological activity of piperdine derivatives, see: Ramalingan et al. (2004 ▶), Weintraub et al. (2003 ▶); Ramachandran et al. (2011 ▶). For a related structure, see: Aridoss et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₁H₂₄ClNO
M _r = 341.86
Triclinic,
a = 7.5488 (6) Å
b = 9.9706 (7) Å
c = 12.9887 (10) Å
α = 106.783 (4)°
β = 93.022 (4)°
γ = 102.347 (4)°
V = 907.45 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.953, T _max = 0.958
13736 measured reflections
3806 independent reflections
3169 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.131
S = 1.02
3806 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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, New_Global_Publ_Block. DOI: 10.1107/S1600536813022289/su2628sup1.cif

e-69-o1424-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022289/su2628Isup2.hkl

e-69-o1424-Isup2.hkl^{(182.8KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813022289/su2628Isup3.cml

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
C7—H7⋯Cl1	0.98	2.68	3.3736 (16)	128
C13—H13⋯O1	0.98	2.27	2.732 (2)	108

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Acknowledgments

SP and SA thank the UGC, New Delhi, for financial assistance in the form of a Major Research Project. The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data collection and computer facilities.

supplementary crystallographic information

1. Comment

The piperidine sub-structure is a ubiquitous structural feature of many alkaloids, natural products and drug candidates (Weintraub et al., 2003). The motivation for biological trials arises as piperidine derivatives are an important class of heterocyclic compounds with potent pharmacological and biological activities (Ramalingan et al., 2004; Ramachandran et al., 2011). We report herein on the synthesis and crystal structure of a new piperidine derivative.

In the title molecule, Fig. 1, the phenyl rings are attached to the piperidine ring in the symmetric position through bonds C6—C7 [1.5252( ) Å] and C13—C14 [1.523( ) Å]. These bond distances are comparable with those in a related structure (Aridoss et al., 2011). The two phenyl rings (A = C1-C6 and B = C14-C19) are inclined to one another by 20.7 (1) °. The sum of the bond angles around the N atom of the piperidine ring (360 °) shows sp³ hybridization. The piperidine ring (C7-C10/C13/N1) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) of Q(2) = 0.0311 (16) Å, φ(2) = 135 (3) ° Q(3) = 0.5222 (16) Å with Puckering Amplitude (Q) = 0.5231 (16) Å, θ = 3.42 (18) °, π = 135 (3) °. The two phenyl rings (A and B) are inclined to the mean plane of the four planar atoms (N1/C13/C9/C8) of piperidine ring by 87.64 (10) and 70.8 (1) °, respectively.

The molecule is stabilized by short intramolecular C—H···Cl and C—H···O contacts (Table 1).

In the crystal, the molecules stack along the c axis direction without any specific interactions (Fig. 2).

2. Experimental

The title compound was synthesized according to the published procedure (Venkatraj et al., 2008). A mixture of piperidine (5 mmol), chloroacetylchloride (20 mmol) and triethylamine (20 mmol) in anhydrous benzene (20 ml) was stirred at rt for 7 h. The precipitated ammonium salt was washed with water (4 × 10 ml) and the benzene solution was dried and concentrated. The pasty mass was purified by crystallization from ethanol giving colourless block-like crystals [M.p. 377-379 K].