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J Chem Crystallogr (2010) 40:437–442
weeds emerge or to the growing plants. The morpholi-
nomethyl derivative of pyrizinamide (morphozinamide)
has been found to be more effective in the treatment of
tuberculosis than pyrizinamide [4].
Experimental
Reagents and Techniques
Succinimide is a diketopyrrolidine that is prepared by
heating succinic anhydride with aqueous ammonia, fol-
lowed by rapid distillation of ammonium succinate [5, 6].
Succinimide and other cyclic carboximides are used as
starting materials in organic synthesis. Their nitranions are
also important intermediates in many chemical reactions
[5–8]. Derivatives of succinimide are of important bio-
logical and pharmacological interest. In addition, succini-
mide itself is a hypooxaluric agent [9]. Succinimide
oxidises in various substrates in different media [10–15].
Extensive work has been reported on the kinetics of oxi-
dation of amino acids and peptides with various metal ions
and several other oxidants [15–17]. The comparative
studies on the kinetics of oxidation of amino acids and
tetrapeptides by N-bromosuccinimide have been reported
[18]. The crystal structures of several succinimide deriva-
tives have been reported with respect to their biological
properties, e.g. antiepileptic and anticonvulsive [19–22],
fungicidal [19] and other pharmacological [23] activities.
In each of these compounds, the ring nitrogen is substituted
either by methyl group, or differently substituted phenyl
and pyridine rings or morpholinomethyl moiety [24]. The
succinimide derivatives are useful as anti-anxiety drugs.
A group of phenylsuccinimides [25, 26] proved to have
strong anticonvulsive activity. A search through the litera-
ture firmly revealed that no work has been carried out on the
synthesis of Mannich bases employing succinimide, mor-
pholine and benzaldehyde as the reactants for condensation.
Therefore it was thought worthwhile to synthesize this
condensation product through Mannich condensation reac-
tion and investigate its molecular structure. Mannich reac-
tion is a three component condensation reaction consisting
of a compound with active hydrogen, an aldehyde (gener-
ally formaldehyde) and a secondary amine [27, 28]. In
continuation with the earlier reported work on the synthesis
of 1-[(2,5-dioxopyrrolidin-1-yl)(phenyl)methyl] urea using
urea, succinimide and benzaldehyde [29], we herein report
the synthesis, spectroscopic studies and crystal structure of
the title compound (Fig. 1).
All the reagents used for synthesizing the title compound
were of A.R Grade and the solvents used were commercial
products of the highest available purity. The micro ele-
mental analysis was carried out with a Carlo Erba 1108
Elemental Analyzer. Infrared spectrum was recorded in
KBr medium on a Spectrum-One Perkin Elmer FTIR
1
instrument. H NMR spectrum was recorded in DMSO-d6
and 13C NMR spectrum was recorded in CDCl3 using a
Bruker 300 MHz instrument. UV–Visible spectrum was
recorded in DMF on a EZ301 Perkin Elmer spectropho-
tometer. FAB Mass spectrum was recorded on a JEOL SX
102 Mass Spectrometer.
Synthesis
Succinimide (19.8 g, 0.2 M), morpholine (18 mL, 0.2 M)
and benzaldehyde (22 mL, 0.2 M) were taken in equimolar
ratio. Morpholine was added slowly to succinimide taken
in a 250 mL beaker. Sufficient amount of ethanol was
added to make the contents a homogeneous solution.
Benzaldehyde was added slowly in drops with continuos
stirring of the solution. A yellowish white powdery sub-
stance was formed immediately. After 10 days the product
was washed several times with distilled water. The product
was dried in the air oven at 60 °C and recrystallised from
ethanol by slow evaporation. Colorless crystals suitable for
X-ray diffraction study were obtained m.p. 100–105 °C,
yield 85.4%. Found: C, 63.68; H, 6.52; N, 10.43. Calc. For
C15H18N2O3; C, 65.69; H, 6.57; N, 10.22%.
Crystallography
A crystal of dimensions 0.40 9 0.28 9 0.22 mm was used
for collection of intensity data on a ‘‘Bruker APEXII
CCD’’ area detector diffractometer with graphite mono-
chromated MoKa radiation (50 kV, 30 mA) using the
APEX2 [30] data collection software. The collection
method involved phi and x-scans of width 0.5° with an
exposure time of 10 s/frame. Data reduction was carried
out using the program SAINT? [31]. The crystal structure
was solved by direct methods using SHELXTL [32]. Non-
hydrogen atoms were first refined isotropically followed by
anisotropic refinement by full matrix least-squares calcu-
lations based on F2 using SHELXTL. Hydrogen atoms
were first located in the difference map then positioned
geometrically and allowed to ride on their respective parent
atoms. Hydrogen atoms involved in hydrogen-bonding
were located in the difference map and refined freely.
Diagrams and publication material were generated using
Fig. 1 The Mannich reaction scheme
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Rajeswari
