Alizapride

Solid

Solid

1: Methyl 4-amino-2-methoxybenzoate is protected by acylation to the amino group, followed by nitration, reduction, nitrosation and cyclization to form a benzotriazole derivative, which is hydrolyzed to remove the protection at position 1. Group, and finally react with 2-aminomethyl-N-allylpyrrolidine to obtain aripipride. Method 2: Direct nitration of 4-amino-2-methoxybenzoic acid methyl ester, then hydrogenation reduction, nitrosation and cyclization to generate benzotriazole derivatives, and then with 2-aminomethyl-N-allylpyrrolidine Respond and get alipride. The last step of the above two methods can directly obtain aripipride hydrochloride as follows: 621g of 6-methoxy-1H-benzotriazole-5-carboxylic acid, 3L of anhydrous toluene and 425Gn-( 1-allyl)-2-aminomethylpyrrolidine was refluxed together for 5h. After cooling to 50°C, 600ml of ethanol solution containing hydrogen chloride (350g hydrogen chloride dissolved in 1L ethanol) was added, and the temperature rose to 70-80°C. After cooling to 50°C and separating the toluene layer, the remaining oily residue was dissolved in 3L methanol and heated until completely dissolved. Filter with 150g activated carbon at its boiling temperature. Add 6L of methyl ethyl ketone to the filtrate, and then cool to 0°C to slowly crystallize alibride. Filter, wash twice with 500ml methyl ethyl ketone, and then dry in a ventilated dryer at 50°C. Finally, 687 g of aripipride hydrochloride was obtained with a yield of 65% and a melting point of 206-208°C.

Antiemetic.

Molecular Weight:315.37
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:315.16952493
Monoisotopic Mass:315.16952493
Topological Polar Surface Area:83.1
Heavy Atom Count:23
Complexity:433
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes