2-[4-(Morpholin-4-ylmeth­yl)phen­yl]benzonitrile

Gangadhar Y Meti; R R Kamble; A J Ravi; H K Arunkashi; H C Devarajegowda

doi:10.1107/S1600536812050957

. 2012 Dec 22;69(Pt 1):o129. doi: 10.1107/S1600536812050957

2-[4-(Morpholin-4-ylmethyl)phenyl]benzonitrile

Gangadhar Y Meti ^a, R R Kamble ^a, A J Ravi ^b, H K Arunkashi ^b, H C Devarajegowda ^b,^*

PMCID: PMC3588350 PMID: 23476389

Abstract

In the title compound, C₁₈H₁₈N₂O, the morpholine ring adopts a chair conformation with the exocyclic N—C bond in an equatorial orientation. The dihedral angles between the central benzene ring and the morpholine ring (all atoms) and the cyanobenzene ring are 87.87 (7) and 52.54 (7)°, respectively. No significant intermolecular interactions are observed in the crystal structure.

Related literature

For biological applications of biphenyl derivatives see; Li et al. (2011 ▶); Hadizad et al. (2009 ▶); Larsen et al. (1994 ▶); Kamble et al. (2011 ▶); Zhang et al. (2004 ▶); Chan et al. (1994 ▶).

Experimental

Crystal data

C₁₈H₁₈N₂O
M _r = 278.34
Monoclinic,
a = 21.1079 (5) Å
b = 8.1358 (1) Å
c = 9.0793 (2) Å
β = 100.833 (1)°
V = 1531.40 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.770, T _max = 1.000
10319 measured reflections
2387 independent reflections
1948 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.083
S = 1.03
2387 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(18.9KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050957/hb7014sup1.cif

e-69-0o129-sup1.cif^{(18.9KB, cif)}

Click here for additional data file.^{(114.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050957/hb7014Isup2.hkl

e-69-0o129-Isup2.hkl^{(114.9KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050957/hb7014Isup3.cml

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

Acknowledgments

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the data collection. The authors are also grateful to University Grants Commission, New Delhi for financial assistance [letter No. 37-248/2009 (SR)].

supplementary crystallographic information

Comment

Biphenyl derivatives were reported as non-peptide A^II antagonists by the discovery at Du-pont Merck which resulted into clinical candidate (5–2-[(4-methyl)-biphenyl]-1H-tetrazole. This has become the common motif for most of the potent antagonists reported (Li et al., 2011; Hadizad et al., 2009; Larsen et al., 1994). This discovery lead to the development of drugs such as irbesartan and losartan for the efficient treatment of hypertension. Since then these biphenyl derivatives have received enormous focus due to their inhibition of angiotensin converting enzyme (ACE) and in this regard many biphenyl derivatives have been reported (Kamble et al., 2011; Zhang et al., 2004; Chan et al., 1994).

The asymmetric unit of 4'-(morpholin-4-ylmethyl)biphenyl-2-carbonitrile is shown in Fig. 1. The the morpholine ring (O1/N2/C4–C7)adopts a chair conformation. The dihedral angle between the morpholine ring (O1/N2/C4–C7) and the benzene rings (C9–C14) and (C15–C20) are 87.87 (7)° and 44.76 (7)° respectively. No significant intermolecular interactions are observed. The crystal packing of the molecules is shown in Fig.2.

Experimental

A mixture of 4'-(bromomethyl)-biphenyl-2-carbonitrile (0.0074 mol), morpholine (0.0085 mol) in presence of potassium carbonate (0.009 mol) in acetone (20 ml) was stirred at 298–300 K for 5–6hrs, filtred the salt, filtrate added to 50 ml water stirred well to get solid, filtered and washed with water, dried at 313 K. Colourless plates were recrystallized from a solvent mixture of acetone and THF (m.p. 348 K).