ChemicalBook CAS DataBase List Aripiprazole

Aripiprazole synthesis

6synthesis methods

Product Name:Aripiprazole
CAS Number:129722-12-9
Molecular formula:C23H27Cl2N3O2
Molecular Weight:448.39

Aripiprazole, sold under the brand name Abilify among others, is an atypical antipsychotic. It is recommended and primarily used in the treatment of schizophrenia and bipolar disorder. Other uses include as an add-on treatment in major depressive disorder, tic disorders, and irritability associated with autism. Aripiprazole is a quinoline derivate and atypical anti-psychotic agent. Aripiprazole has partial agonistic activity at dopamine D2 receptors and serotonin 5-HT1A receptors, as well as potent antagonistic activity on serotonin 5-HT2A receptors.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Shi, Hang; Babinski, David J.; Ritter, Tobias. Modular C-H Functionalization Cascade of Aryl Iodides. Journal of the American Chemical Society. Volume 137. Issue 11. Pages 3775-3778. 2015.

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Yield:129722-12-9 99.3%

Reaction Conditions:

at 100 - 120; for 21 h;Industrial scale;

Steps:

1 Example 1

Example 1
The aripiprazole hydrate A (powder) (44.29 kg) obtained in the Reference Example 4 was dried at 100° C. for 18 hours by using a hot air dryer and further heated at 120° C. for 3 hours, to obtain 42.46 kg (yield; 99.3%) of Anhydrous Aripiprazole Crystals B. These Anhydrous Aripiprazole Crystals B had a melting point (mp) of 139.7° C.
The Anhydrous Aripiprazole Crystals B obtained above had an ¹H-NMR spectrum (DMSO-d₆, TMS) which was substantially identical to the ¹H-NMR spectrum shown in .
Specifically, they had 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+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).
The Anhydrous Aripiprazole Crystals B obtained above had a powder x-ray diffraction spectrum which was substantially the identical to the powder x-ray diffraction spectrum shown in .
Specifically, they had characteristic peaks at 2θ=11.0°, 16.6°, 19.3°, 20.3° and 22.1°.
The Anhydrous Aripiprazole Crystals B obtained above had remarkable infrared absorption bands at 2945, 2812, 1678, 1627, 1448, 1377, 1173, 960 and 779 cm^-1 on the IR (KBr) spectrum.

References:

US9387182,2016,B2 Location in patent:Page/Page column 17

120004-79-7 Synthesis