2,2-Diphenyl-4-(piperidin-1-yl)butanamide

M S Siddegowda; Jerry P Jasinski; James A Golen; H S Yathirajan; M T Swamy

doi:10.1107/S1600536811024585

. 2011 Jun 25;67(Pt 7):o1827. doi: 10.1107/S1600536811024585

2,2-Diphenyl-4-(piperidin-1-yl)butanamide

M S Siddegowda ^a, Jerry P Jasinski ^b,^*, James A Golen ^b, H S Yathirajan ^a, M T Swamy ^c

PMCID: PMC3151741 PMID: 21837195

Abstract

In the title compound, C₂₁H₂₆N₂O, the dihedral angle between the mean planes of the two benzene rings is 81.1 (9)°. The piperidine ring is in a chair conformation. The crystal packing is stabilized by N—H⋯N and N—H⋯O hydrogen bonds and weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity and pharmaceutical applications of compounds similar to the title compound, see: Guzel et al. (2006 ▶). For related structures, see: Akkurt et al. (2007 ▶); Dutkiewicz et al. (2010 ▶); Gerkin (1998 ▶); Krigbaum et al. (1968 ▶); Narasegowda et al. (2005 ▶); Yathirajan et al. (2005 ▶). For standard bond lengths, see Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₁H₂₆N₂O
M _r = 322.44
Orthorhombic,
a = 18.1070 (12) Å
b = 10.3025 (9) Å
c = 9.6150 (6) Å
V = 1793.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.40 × 0.32 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.971, T _max = 0.986
19279 measured reflections
4817 independent reflections
4547 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.102
S = 1.02
4817 reflections
224 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024585/sj5167sup1.cif

e-67-o1827-sup1.cif^{(21KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024585/sj5167Isup2.hkl

e-67-o1827-Isup2.hkl^{(236KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024585/sj5167Isup3.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
N1—H1NB⋯N2ⁱ	0.87 (1)	2.08 (1)	2.9457 (13)	177 (2)
N1—H1NA⋯O1ⁱⁱ	0.84 (1)	2.38 (1)	3.1971 (14)	164 (2)
C3—H3B⋯O1ⁱⁱ	0.99	2.47	3.3738 (14)	152

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

Acknowledgments

MSS thanks the University of Mysore for research facilities and HSY thanks R. L. Fine Chem, Bangalore, India, for the gift sample. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

The title compound is an intermediate used in the synthesis of biologically and pharmaceutically active compounds viz., loperamide, darifenacin, fenpiverine, etc. The synthesis and antimycobacterial activity of some new related 2,2-diphenylacetamide derivatives has been described (Guzel et al., 2006). The crystal structures of N,N-diphenylacetamide (Krigbaum et al., 1968), 4,4'-dimethylbiphenyl-2,2'-dicarboxylic acid (Gerkin, 1998), 4'-methylbiphenyl-2-carboxylic acid (Narasegowda et al., 2005) and 4'-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl) biphenyl-2-carbonitrile (Yathirajan et al., 2005), 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide (Akkurt et al., 2007) and 2-chloro-N-[4-chloro-2-(2-chlorobenzoyl) phenyl]acetamide (Dutkiewicz et al., 2010) have been reported. In view of the importance of the title compound, (I), C₂₁H₂₆N₂O, a new crystal structure determination is reported.

In the title compound, (I), the dihedral angle between the mean planes of the two benzene rings is 81.1 (9)° (Fig. 1). The piperidin-1-yl ring is in a chair conformation (Cremer & Pople (1975), puckering parameters Q, θ, and φ = 0.5689 (15)A%, 3.89 (16)° and 14 (2)° respectively). For an ideal chair θ has a value of 0 or 180°. Bond lengths are normal (Allen et al., 1987). Crystal packing is stabilized by N—H···N, N—H···O hydrogen bonds and weak C—H···O intermolecular interactions (Fig. 2, Table 1).

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of (1:1) methanol and dichloromethane solution (m.p.: 458-460 K).