1-Chloro-2-(4-phenyl­piperazin-1-yl)ethanone

Yong-Ji Xu; Fei Jing

doi:10.1107/S1600536809008216

. 2009 May 7;65(Pt 6):o1211. doi: 10.1107/S1600536809008216

1-Chloro-2-(4-phenylpiperazin-1-yl)ethanone

Yong-Ji Xu ^a,^*, Fei Jing ^a

PMCID: PMC2969821 PMID: 21583080

Abstract

The title compound, C₁₂H₁₅ClN₂O, is a piperazine derivative with the potential for use as a starting material for pharmaceutial and agrochemical applications. The structure is stabilized by C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = is 4.760 (2) Å].

Related literature

For the biological activity of piperazine and its derivatives, see: Berkheij (2005 ▶); Upadhayaya et al. (2004 ▶); Choudhary et al. (2006 ▶); Vacca et al. (1994 ▶); Hulme (1999 ▶). For reference structural data, see: Drew & Leslie (1986 ▶).

Experimental

Crystal data

C₁₂H₁₅ClN₂O
M _r = 238.71
Monoclinic,
a = 9.4423 (19) Å
b = 8.5629 (17) Å
c = 14.506 (3) Å
β = 101.34 (3)°
V = 1149.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.940, T _max = 0.964
9264 measured reflections
2729 independent reflections
2151 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.07
2729 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks I, global. DOI: 10.1107/S1600536809008216/hg2461sup1.cif

e-65-o1211-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008216/hg2461Isup2.hkl

e-65-o1211-Isup2.hkl^{(134KB, 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
C2—H2⋯O1ⁱ	0.93	2.47	3.1850 (16)	134
C9—H9A⋯O1	0.97	2.38	2.7456 (17)	102
C12—H12B⋯O1ⁱⁱ	0.97	2.43	3.3426 (16)	157
C5—H5⋯Cg2ⁱⁱⁱ	0.93	3.25	3.7651 (15)	117
C8—H8B⋯Cg2^iv	0.97	3.09	4.0393 (12)	168
C12—H12A⋯Cg2^iv	0.97	3.04	3.6878	125

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C1–C6 ring.

Acknowledgments

This work was supported by the Natural Science Foundation of Shandong Province, China (No. Y2007B50). The authors thank Professor Yong-Hong Wen for help with this paper.

supplementary crystallographic information

Comment

Piperazine and its derivatives are important pharmacores that can be found in biologically active compounds across a number of different therapeutic areas (Berkheij, 2005), such as antifungal (Upadhayaya et al., 2004), anti-bacterial, anti-malarial, anti-psychotic agents (Choudhary et al., 2006), HIV protease inhibitor (Vacca et al., 1994), anti-depressant and anti-tumour activity colon, prostate, breast, lung and leukemia tumors (Hulme et al., 1999). In an attempt to further synthesis piperazine derivatives, the title compound, 2-chloro-1-(4-phenylpiperazin-1-yl)ethanone, (I) (Fig. 1), was synthesized and its X-ray crystal structure determined.

In the structure of title compund (Fig. 1), the bond lengths and angles in the piperazine ring and the benzene ring are normal (Drew & Leslie, 1986) (Table 1). The dihedral angle between the piperazine ring N1/N2/C7—C10 and C1—C6 benzene ring is 36.8 (2)°. The molecular structure is stabilized by inter and intramolecular C—H···O interactions (Table 2). There exists π-π stacking interactions and C—H···π interactions. The π-π stacking interaction between the two phenyl rings is observed in the structure. The centroid distance between the two rings is 4.760 Å. There are three types of C—H···π interactions, C5—H5···C_g2, C8—H8B···C_g2 and C12—H12A···C_g2 (C_g2 is the C1—C6 ring centroid) (Table 2).

Experimental

To a solution of 1-phenylpiperazine hydrochloride (2.0 g, 10 mmol) triethylamine (2.8 ml, 2 mmol) in anhydrous dichloromethane (50 ml) was added chloroacetyl chloride (0.8 mL, 10 mmol) dropwise at 273 K. The reaction mixture was stirred at room temperature for 2 h and monitored by TLC, and then the mixture was diluted with dichloromethane (50 ml) and washed with water (200 ml). The organic phase was dride over anhydrous sodium sulfate and concentrated to yield a solid which was crystallized to obtain 2-chloro-1-(4-phenylpiperazin-1-yl)ethanone.