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Monday, 25 November 2013

Aripiprazole spectral data

Aripiprazole2D1.svg
Aripiprazole

A mixture of 7-(4-Bromobutoxy)-2(1H)-quinolinone (297 g, 1.0 mol), NaI (234 g, 1.56 mol),
triethylamine (173.7 g, 1.72 mol) and 1-(2, 3-dichlorophenyl)-piperazine hydrochloride (381
g, 1.43 mol), in acetonitrile (750 mL) was refluxed for 4 h with stirring. Progress of reaction
was monitored by TLC; using benzene: ethyl acetate (7:3) solvent system. The reaction
mixture was filtered, and the filtrate was evaporated to dryness in vacuo. The residue was
extracted with CHCl3, and the extract was washed, dried, and evaporated in vacuo.
Recrystallization from MeOH-CHCl3 gave the desired product as colorless needles. Product
Yield: 407.0 g, 84 %

http://jocpr.com/vol2-iss5-2010/JCPR-2010-2-5-506-517.pdf



IR
3368 (N-H stretching),
3109 (aromatic C-H stretching),
2944(aliphatic C-H stretching),
1677 (C=O stretching),
1594-1445(aromatic region),
1174 (C-N stretching),
779 (C-Cl stretching).

NMR
ð 1.77-1.72 ppm (t, 2H, -CH2),
1.83-1.79 (t, 2H, -CH2),
2.50-2.45(t, 2H, -CH2),
2.63-2.58 (m, 6H, CO-CH2-CH2 of carbostyryl,CH2 of piperazine),
2.91-2.86 (m, 2H, -CH2 of piperazine),
3.06(s, 4H, -CH2 of piperazine),
6.30-6.29 (s, 1H, -ArH),
6.53-6.50 (dof d, 1H,-ArH),
6.98-6.93 (m, 1H, -ArH),
7.05-7.02 (d, 1H, -ArH),
7.16-7.10 (d, 2H, -ArH),
7.79 (s, 1H, -NH)






1H NMR spectrum of Aripiprazole (CDCl3, 298 K, 600 MHz): 8.52 (s,1H),
7.14-7.15 (m,2H), 7.04 (d,1H,J=8.30 Hz), 6.96 (dd,1H,J=7.10,2.52Hz), 6.52
(dd,1H,J=8.30,2.30 Hz), 6.36 (d,1H,J=2.30 Hz), 3.96 (t,2H,J=6.25 Hz), 3.07 (m,4H), 2.89
(t,2H,J=7.50 Hz), 2.65 (m,4H), 2.62 (t,2H,J=7.50 Hz), 2.48 (t,2H,J=7.55 Hz), 1.82
(m,2H), 1.71 (m,2H).


1H-NMR spectral data of Aripiprazole (DMSO-d6, 298 K, 600 MHz): 9.98 
(s,1H), 7.28-7.30 (m,2H), 7.12 (dd,1H,J=7.10,2.35 Hz), 7.04 (d,1H,J=8.30 Hz), 6.48 
(dd,1H,J=8.30,2.35 Hz), 6.45 (d,1H,J=2.35 Hz), 3.96 (t,2H,J=6.45 Hz), 2.97 (m,4H), 2.78 
(t,2H,J=7.45 Hz), 2.52 (m,4H), 2.41 (t,2H,J=7.45 Hz), 2.38 (t,2H,J=7.15 Hz), 1.72 
(m,2H), 1.58 (m,2H)

1H NMR spectrum of Aripiprazole (CD3OH, 298 K, 500 MHz): 9.80 (bs,1H), 
7.18-7.24 (m,2H), 7.02-7.09 (m,2H), 6.54 (dd,1H,J=8.25,2.45 Hz), 6.44 (d,1H,J=2.49 
Hz), 3.97 (t,2H,J=6.15 Hz), 3.06 (m,4H), 2.85 (t,2H,J=7.35 Hz), 2.67 (m,4H), 2.47-2.54 
(m,4H), 1.79 (m,2H), 1.73 (m,2H). 

  1. Sixth polymorph of Aripiprazole - an antipsychotic drug.

    www.rsc.org/suppdata/ce/c2/c2ce25306b/c2ce25306b.pdf‎

    H NMR spectrum of Aripiprazole (CDCl3, 298 K, 600 MHz): 8.52 (s,1H),. 7.14-7.15 (m,2H), 7.04 (d,1H,J=8.30 Hz), 6.96 (dd,1H,J=7.10,2.52Hz), 6.52. (dd,1H ...


    Spectroscopic studies of aripiprazoleDownload the full textDownload the full text
    Author:Li Jianfeng 1, Liu Aixiang 1, Xia Guang-xin 1, 2, was also abundant, Shen Jing Shan 1 *
    Journal Name:Spectroscopy and Spectral Analysis
    Title:200 727 (05)
    Post time:2006.12.18
    Download URL:www.gpxygpfx.com/qikan/manage/wenzhang/2007-05-0863.pdf

    http://www.gpxygpfx.com/qikan/manage/wenzhang/2007-05-0863.pdf

Aripiprazole (7-[4-[4- (2,3-dichlorophenyl) piperazin-1-yl] butoxy]-3,4- dihydro- 1H quinolin-2-one) is an anti - psychotic drug.






1H-NMR spectrum (DMSO-d6, TMS) shown in FIG. 23. Specifically, it has characteristic peaks at 1.55-1.63 ppm (m, 2H), 1.68-1.78 ppm (m, 2H), 2.35-2.46 ppm (m, 4H), 2.48-2.56 ppm (m, 4H 4-DMSO), 2.78 ppm (t, J=7, 4 Hz, 2H), 2.97 ppm (brt, J=4.6 Hz, 4H), 3.92 ppm (t, J=6.3 Hz, 2H), 6.43 ppm (d, J=2.4 Hz, 1H), 6.49 ppm (dd, J=8.4 Hz, J=2.4 Hz, 1H), 7.04 ppm (d, J=8.1 Hz, 1H), 7.11-7.17 ppm (m, 1H), 7.28-7.32 ppm (m, 2H) and 10.00 ppm (s, 1H);
 IR (KBr) spectrum shown in FIG. 21. Specifically, it has clear infrared absorption bands at 2943, 2817, 1686, 1377, 1202, 969 and 774 cm−1.
HPLC purity: 99.39%, Methanol content: 6.57% Elemental analysis: C: 59.88%, H: 6.60%, N: 8.62% and calculated values for C2IH3ICl2N3O3. C: 59.95%, H: 6.45%, N: 8.74%
IR Spectrum (KBr, cm-1): 3196, 3108, 2948, 2819, 1675, 1628, 1595, 1578, 1522, 1449, 1378, 1335, 1274, 1243, 1197, 1173, 1140, 1127, 1040, 997, 960, 859, 830, 809, 784, 748, 713 and 532.
1H NMR (300 MHz, CDCl3, ppm) : 1.65 - 1.85 («ι, 4H), 2.49 (t, 2H), 2.51 (t, 2H), 2.59 - 2.64 (m, 4H), 2.89 (t, 2H), 3.08 (m, 4H), 3.49 (s, 3H),
3.97 (t, 2H), 6.32 (d, IH), 6.51- 6.54 (dd, IH), 6.94 - 6.97 (m, IH), 7.05 (d, IH), 7.11 - 7.17 (m, 2H), 8.04 (s, IH).
13C NMR (300 MHz, DMSO-d6, ppm): 23.19, 24.38, 27.14, 30.90, 50.17, 51.08, 53.12, 58.07, 67.7, 102.2, 108.7, 115.5, 118.5, 124.39, 127.31, 127.34, 128.4, 133.8, 138.1, 151.1, 158.5 and 172.41.
Mass Spectrum (M+): 448.2, 285.1/ 218.1, 176.0, and 164.1. The XRD shows the peaks at 9.4, 10.7, 11.4, 11.8, 12.3, 13.3, 17.3, 18.4, 19.8, 23.3, 24.3, 25.6, 26.8, 28.0, 28.9, 31.2° + 0.2 2 theta values

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