ChemicalBook CAS DataBase List acepromazine

acepromazine synthesis

8synthesis methods

Product Name:acepromazine
CAS Number:61-00-7
Molecular formula:C19H22N2OS
Molecular Weight:326.46

6631-94-3
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109-54-6 Synthesis

109-54-6
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61-00-7
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Yield: 22%

Reaction Conditions:

Stage #1:2-acetylphenothiazine with sodium hydride in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2:3-(Dimethylamino)propyl chloride in N,N-dimethyl-formamide at 50; for 5 h;

Steps:

General procedure for the synthesis of phenothiazine derivatives 17-21
General procedure: To a solution of 2-acetylphenothiazine (1 mmol) inanhydrous DMF (12 mL) was added NaH (4.5 eq) in portions, and the mixture wasstirred for 30 min at room temperature. Then, the correspondingchloro-derivatives 77-81 were added, and the mixture wasstirred for 5 hours at 50°C. The solution was then concentratedunder vacuum and the residue was purified through column chromatography(7.3:0.2:2.5:0.02 DCM/ethanol/toluene/NH₃).

References:

Bolognesi, Maria Laura;Carloni, Paolo;Colini Baldeschi, Arianna;Gandini, Annachiara;Legname, Giuseppe;Rossetti, Giulia;Salzano, Giulia;Tran, Thanh Hoa;Zaccagnini, Ludovica [European Journal of Medicinal Chemistry,2020,vol. 196] Location in patent:supporting information