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ChemicalBook CAS DataBase List PAROXETINE-D4 HCL

PAROXETINE-D4 HCL synthesis

13synthesis methods

Product Name:PAROXETINE-D4 HCL
CAS Number:110429-35-1
Molecular formula:C19H23ClFNO4
Molecular Weight:383.84

253768-88-6 Synthesis

253768-88-6
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110429-35-1
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Yield:110429-35-1 97%

Reaction Conditions:

Stage #1: (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylic acid phenyl esterwith potassium hydroxide in sulfolane;toluene at 80 - 85; for 4 h;
Stage #2: with water in sulfolane;toluene at 30 - 35;
Stage #3: with hydrogenchloride in water;toluene at 20 - 25; for 2 h;Product distribution / selectivity;

Steps:

6

Example 6:; Preparation of (-)-*r??s-4-(4-fluoropheny)-3-[[3,4-(methyIenedioxy)phenoxy] methyLJpiperidine, compound of formula I; A mixture of compound of formula II (1Og), toluene (50ml), sulfolane (10ml) and potassium hydroxide (6g) is heated to 80-85⁰C for 4hrs, cooled to 30-35⁰C and then quenched by addition of water (30ml) at 30-35⁰C. The upper toluene layer was separated and the aqueous layer extracted with toluene (20ml). The combined toluene layer were washed successively with water and saturated aqueous sodium chloride solution, charcoalized and acidified with cone, hydrochloric acid. After stirring at 20-25⁰C for 2hrs the product was filtered and washed with toluene followed by water. The product was dried to constant weight to yield paroxetine hydrochloride hemihydrate, as a white crystalline solid, 8. Ig (97% yield), purity 99.87% by HPLC.

References:

WO2007/15262,2007,A2 Location in patent:Page/Page column 18