382 Verma et al.
Asian J. Chem.
NHCOCH2Cl
NH2
C OCl
(4.5:0.5) and spots were visualized in an iodine chamber. The
mixture was then poured into crushed ice. The solid product
so obtained was washed with aq. NaOH followed by water.
General procedure for the synthesis of N-(2-benzoyl-
4-chlorophenyl)-2-chloracetamide derivatives (SA1-SA7):
N-(2-Benzoyl-4-chlorophenyl)-2-chloracetamide derivatives
were prepared by stirring the equimolar of N-(2-benzoyl-4-
chlorophenyl)-2-chloracetamide and different substituted
arylpiperazine derivatives in the presence of double mole of
potassium carbonate in a minimum quantity of DMF at room
temperature for 20-28 h. After that the reaction mixture was
poured into ice cold water and the solid product thus separated
was collected through filtration.
Toluene
Reflux
ClCOCH2Cl
Cl
Cl
CCl4
AlCl3
Abs. ethanol
NHCOCH2R1
NHCOCH2Cl
K2CO3, DMF
O
O
Stirring for 24-28 h
2-[4-(Phenyl)piperazin-1-yl]acetamido-5-chlorobenzo-
phenone (SA1): IR (KBr, νmax, cm-1): 3240 (NH amide), 3047
(CH, arom.), 2921 (CH aliph.), 1703 (C=O ketone), 1645 (C=O
amide), 1284 (C-N arom.), 1236 (C-N aliph.), 748 (C-Cl). 1H
NMR (300 MHz; CDCl3, δ): 2.77-3.39 (m, 8H, pip. ring), 3.25
(s, 2H,CH2CO), 6.89-8.68 (m, 13H,Ar-H), 11.55 (s, 1H, NH).
13C NMR (CDCl3, δ): 196.47, 169.89, 151.14, 137.50, 133.17,
133.02, 131.77, 130.09, 129.10, 128.50, 127.52, 126.31,
123.06, 119.66, 116.11, 62.28, 77.21, 76.79, 53.51, 48.92.
2-[4-(2-Methylphenyl)piperazin-1-yl]acetamido-5-
chlorobenzophenone (SA2): IR (KBr, νmax, cm-1): 3234 (NH
amide), 3058 (CH, arom.), 2929 (CH aliph.), 1693 (C=O
ketone), 1650 (C=O amide), 1282 (C-N arom.), 1240 (C-N
aliph.), 746 (C-Cl). 1H NMR (300 MHz; CDCl3, δ): 2.77-3.91
(m, 8H, pip. ring), 3.25 (s, 2H, CH2CO), 3.88 (s, 3H, CH3),
6.89-8.67 (m, 12H, Ar-H), 11.52 (s, 1H, NH). 13C NMR
(CDCl3, δ): 195.36, 170.12, 151.22, 141.19, 137.59, 137.45,
133.09, 133.02, 131.64, 130.09, 130.07, 128.51, 127.49,
126.47, 123.11, 122.91, 120.91, 118.34, 111,17, 62.34, 77.35,
76.67, 52.34, 53.77.
Cl
Cl
SA1-SA7
where R1
HN
=
H3C
HN
N
N
SA1
SA2
CH3
HN
Cl
H3C
CH3
N
H N
N
N
SA3
SA4
Cl
Cl
HN
HN
N
2-[4-(3-Methylphenyl)piperazin-1-yl]acetamido-5-
chlorobenzophenone (SA3): IR (KBr, νmax, cm-1): 3236 (NH
amide), 3050 (CH, arom.), 2929 (CH aliph.), 1697 (C=O
ketone), 1650 (C=O amide), 1282 (C-N arom.), 1240 (C-N
aliph.), 746 (C-Cl). 1H NMR (300 MHz; CDCl3, δ): 2.77-3.91
(m, 8H, pip. ring), 3.25 (s, 2H, CH2CO), 3.88 (s, 3H, CH3),
6.80-8.61 (m, 12H, Ar-H), 11.52 (s, 1H, NH). 13C NMR
(CDCl3, δ): 196.36, 170.12, 152.22, 141.19, 137.59, 137.45,
133.09, 133.02, 131.64, 130.09, 130.07, 128.51, 127.49,
126.47, 123.11, 122.91, 120.91, 118.34, 111,17, 62.34, 77.35,
76.67, 52.34, 53.77.
SA5
SA6
Cl
Cl
HN
N
SA7
Fig. 1. Synthesis of 2-[4-(aryl substituted)piperazin-1-yl]acetamido-5-
chlorobenzophenone derivatives
ally added with stirring. The mixture was allowed to reflux
for 6-7 h to expel most of the formed HCl. The completion of
reaction was indicated by TLC using silica gel G as stationary
phase and toulene:ethyl acetate (4.5:0.5). It was then cooled
to room temperature and washed with ice cold aqueous ammonia
solution, dried with anhydrous sodium sulfate, filtered and
concentrated in vacuum. The recrystallization of the product
was carried out with alcohol which gives 82 % of product.
N-(2-Benzoyl-4-chlorophenyl)-2-chloracetamide:
2-Chloro-N-(4-chlorophenyl)acetamide was dissolved in CCl4
and then mixed with benzoyl chloride in equimolar quantity.
Finely powdered anhydrous aluminum chloride was added
with frequent shaking during 10 min to the contents of the flask.
The mixture was allowed to reflux for 8-9 h. The reaction’s
progress was monitored by thin layer chromatography (TLC)
using silica gel G using the solvent system toulene:ethyl acetate
2-[4-(2,3-Dimethylphenyl)piperazin-1-yl]acetamido-5-
chlorobenzophenone (SA4): IR (KBr, νmax, cm-1): 3234 (NH
amide), 3058 (CH, arom.), 2929 (CH aliph.), 1693 (C=O ketone),
1650 (C=O amide), 1282 (C-N arom.), 1240 (C-N aliph.), 746
1
(C-Cl). H NMR (300 MHz; CDCl3, δ): 2.77-3.91 (m, 8H,
pip. ring), 3.25 (s, 2H, CH2CO), 3.86 (s, 3H, CH3), 3.45 (s,
3H, CH3), 6.77-8.57 (m, 11H, Ar-H), 11.52 (s, 1H, NH). 13C
NMR (CDCl3, δ): 196.36, 170.12, 152.22, 141.19, 137.59,
137.45, 133.09, 133.02, 131.64, 130.09, 130.07, 128.51,
127.49, 126.47, 123.11, 122.91, 120.91, 118.34, 111,17, 62.34,
77.35, 76.67, 52.34, 53.77.
2-[4-(2-Chlorophenyl)piperazin-1-yl]acetamido-5-
chlorobenzophenone (SA5): IR (KBr, νmax, cm-1): 3239 (NH
amide), 3045 (CH arom.), 2921 (CH aliph.), 1703 (C=O ketone),
1645 (C=O amide), 1284 (C-N arom.), 1236 (C-N ali), 748