5-Methyl-3,3-bis­(4-methyl­piperazin-1-yl)-1-[2-(4-methyl­piperazin-1-yl)eth­yl]indolin-2-one

Hui-Hui Lin; Xiao-Lin Zheng; Sheng-Li Cao

doi:10.1107/S1600536812022416

. 2012 May 23;68(Pt 6):o1855. doi: 10.1107/S1600536812022416

5-Methyl-3,3-bis(4-methylpiperazin-1-yl)-1-[2-(4-methylpiperazin-1-yl)ethyl]indolin-2-one

Hui-Hui Lin ^a, Xiao-Lin Zheng ^a, Sheng-Li Cao ^a,^*

PMCID: PMC3379422 PMID: 22719620

Abstract

In the title compound, C₂₆H₄₃N₇O, each piperazine ring adopts a chair conformation. Two 1-methylpiperazine rings bond to one Csp ³ of the pyrrole ring via the piperazine N atoms, while the third one links to the N atom of the indolin-2-one unit through a flexible ethyl group with an almost syn conformation. In the crystal, molecules are connected through methylene–carbonyl C—H⋯O interactions into an infinite chain along the c axis. The almost parallel arrays are stacked, forming a three-dimensional framework.

Related literature

For the background to indoline-2,3-dione and its derivatives, see Chiyanzu et al. (2005 ▶); Solomon et al. (2009 ▶); Sriram et al. (2004 ▶). For a related structure, see: Lin et al. (2012 ▶).

Experimental

Crystal data

C₂₆H₄₃N₇O
M _r = 469.67
Monoclinic,
a = 15.9433 (8) Å
b = 14.4097 (6) Å
c = 12.5310 (6) Å
β = 108.774 (3)°
V = 2725.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.33 × 0.21 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.613, T _max = 0.746
17378 measured reflections
4785 independent reflections
3332 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.129
S = 1.03
4785 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022416/zj2076sup1.cif

e-68-o1855-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022416/zj2076Isup2.hkl

e-68-o1855-Isup2.hkl^{(234.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022416/zj2076Isup3.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
C19—H19B⋯O1ⁱ	0.97	2.64	3.388 (2)	135

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (project No. 20972099) and the Beijing Municipal Commission of Education (project No. KZ201210028035) for financial support.

supplementary crystallographic information

Comment

Mannich base derivatives of indoline-2,3-dione (isatin) exhibit antibacterial (Chiyanzu et al., 2005), anti-HIV (Sriram et al., 2004) and anticancer activity (Solomon et al., 2009).Recently, we obtained an isatin derivative with an flexible ethylene linker between the N atom of the isatin moiety and the amine group of the morpholine through the reaction of 1-(2-bromoethyl)-5-methylindoline-2,3-dione with excess of morpholine, namely 5-methyl-3,3-bis(morpholin-4-yl)-1-[2(morpholin-4-yl)ethyl] -2,3-dihydro-1H-indol-2-one. As a continue research on the synthesis of indole-2,3-dione(isatin) derivatives, herein we report the synthesis and crystal structure of a new compound based on indoline-2,3-dione through the reaction of 1-(2-bromoethyl)-5-methylindoline-2,3-dione with 1-methylpiperazine, namely 5-methyl-3,3-bis(4-methylpiperazin-1-yl)-1-(2-(4-methylpiperazin-1-yl)ethyl) indolin-2-one.

In the title compound, each piperazine ring adopts a chair conformation. Two 1-methylpiperazine rings bond to one C8(sp³) of the pyrrole ring via the piperazine N atoms (N2, N6), while the third one links to the N1 atom of indolin-2-one moiety through a flexible ethyl group with an almost syn conformation (N1-C15-C16-N5 torsion angle of 58.0 (3)°, as shown in Fig. 1). This steric configuration is similar to that of 5-methyl-3,3-bis(morpholin-4-yl)-1-[2(morpholin-4-yl)ethyl] -2,3-dihydro-1H-indol-2-one (59.7 (3)°) reported by us recently (Lin et al., 2012). Through C19—H19b(methylene)···O2ⁱ(carbonyl) interactions(see Table 1), the molecules are interconnected and arranged into an array along the c direction (i x, -y + 0.5, z +0.5), as shown in Fig. 2. The almost parallel arrays are stacked to form a three-dimensional framework (Fig. 3)

Experimental

To a solution of 1-(2-bromoethyl)-5-methylindoline-2,3-dione (0.27 g, 1 mmol) in N,N-dimethylformamide (5 ml) was added dropwise 1-methylpiperazine (0.60 g, 6 mmol). The mixture was stirred at 80–90°C for 3 h. The colorless crystals of the title compound were deposited by evaporation of the resulting solution in room temperature for one day (m.p. 401.2–403.0 K; yield 45%).