N-Isopropyl­benzamide

Erik M van Oosten; Alan J Lough; Neil Vasdev

doi:10.1107/S1600536808012804

. 2008 May 7;64(Pt 6):o1005. doi: 10.1107/S1600536808012804

N-Isopropylbenzamide

Erik M van Oosten ^a, Alan J Lough ^a,^*, Neil Vasdev ^b

PMCID: PMC2961603 PMID: 21202531

Abstract

In the title compound, C₁₀H₁₃NO, the dihedral angle between the amide group and the phenyl ring is 30.0 (3)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link molecules into one-dimensional chains along the a axis.

Related literature

For related literature, see: Clayden et al. (2006 ▶); Kopka et al. (2005 ▶); Smart (2001 ▶); Van Waarde et al. (2004 ▶); Stephenson, Wilson et al. (2008 ▶); Stephenson, van Oosten et al. (2008 ▶).

Experimental

Crystal data

C₁₀H₁₃NO
M _r = 163.21
Monoclinic,
a = 5.0093 (7) Å
b = 10.1250 (13) Å
c = 9.6714 (14) Å
β = 104.133 (7)°
V = 475.68 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 150 (1) K
0.14 × 0.13 × 0.08 mm

Data collection

Bruker Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing 1995 ▶) T _min = 0.954, T _max = 0.996
2462 measured reflections
887 independent reflections
621 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.148
S = 1.06
887 reflections
114 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012804/hb2729sup1.cif

e-64-o1005-sup1.cif^{(14KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012804/hb2729Isup2.hkl

e-64-o1005-Isup2.hkl^{(44KB, 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
N1—H1N⋯O1ⁱ	0.83 (5)	2.10 (5)	2.890 (5)	160 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Karin A. Stephenson, Dr Andrei K. Yudin and Dr Alan A. Wilson for helpful discussions. We thank Dr Sylvain Houle for allowing the CAMH PET Centre facilities to be used for this research. Financial support for this work was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC) and the Canadian Institutes for Health Research in the form of a Collaborative Health Research Projects Grant (CHRPJ 322787-06).

supplementary crystallographic information

Comment

The isopropylamine moiety is a common structural feature in many pharmaceutical compounds, in particular among β-adrenergic receptor antagonists (β-blockers) (Van Waarde et al., 2004; Kopka et al., 2005). Recent work in our laboratory (Stephenson, Wilson et al., 2008; Stephenson, van Oosten et al., 2008) and others (Van Waarde et al., 2004; Kopka et al., 2005) has focused on developing β-blockers labeled with the positron emitting isotope fluorine-18 (t_1/2 = 109.7 min) at the isopropyl moiety for medical imaging with positron emission tomography. It is established that substitution of fluorine into a drug often enhances its biological properties (Smart, 2001). Our goal is to structurally characterize the isopropylamine group for comparison with fluorinated analogs developed in our laboratory. Herein we report the single-crystal X-ray structure of the title compound, (I), (Fig. 1).

The dihedral angle between the essentially planar set of atoms C7/O1/N1/C8 [r.m.s. deviation 0.006 Å] and the benzene ring (C1–C6) in (I) is 30.0 (3)°. In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into one-dimensional chains along the a axis (Table 1, Fig. 2).

Experimental

N-Isopropylbenzamide was made according to a literature procedure (Clayden et al., 2006), with minor modifications. Benzoyl chloride (0.825 ml, 7.11 mmol) was added to CH₂Cl₂ (17 ml, 0.4 M) under nitrogen. The mixture was cooled in an ice bath to 273 K and stirred for 10 min. Isopropylamine (1.8 ml, 21.33 mmol) was added dropwise. Upon completion of this addition the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. When the starting material was consumed (monitored by TLC) the reaction mixture was diluted with H₂O (150 ml), extracted with CH₂Cl₂ (3 × 50 ml), washed with H₂O (2 × 100 ml) followed by brine (2 × 100 ml), dried over Na₂SO₄, and concentrated. No further purification was necessary. Colourless blocks of (I) were obtained by slow evaporation of a solution of the title compound in CDCl₃. ¹H NMR (CDCl₃, 300 MHz) d = 7.78–7.67 (m, 2H), 7.51–7.36 (m, 3H), 5.99 (br, 1H), 4.37–4.18 (m, 1H), 1.25 (d, J = 6.5 Hz, 6H) ¹³C NMR (CDCl₃, 75 MHz) d = 166.9, 135.2, 131.5, 128.7, 127.0, 42.1, 23.1.