ChemicalBook CAS DataBase List Duloxetine IMpurity A

Duloxetine IMpurity A synthesis

6synthesis methods

Product Name:Duloxetine IMpurity A
CAS Number:947686-09-1
Molecular formula:C25H23NO3S
Molecular Weight:417.52

132335-46-7 Synthesis

(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

132335-46-7
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1885-14-9 Synthesis

1885-14-9
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947686-09-1
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Yield:947686-09-1 75.6%

Reaction Conditions:

Stage #1: N-methyl-(S)-duloxetinewith N-ethyl-N,N-diisopropylamine in toluene at 45; for 0.166667 h;
Stage #2: phenyl chloroformate at 55; for 2 h;

Steps:

A mixture of residue 4 obtained above in toluene (250mL) was stirred for 10min. The temperature was increased at 45°C and diisopropylethyl-amine (7.5g) was added with stirring for further 10min. Subsequently, phenyl chloroformate (52.8g, 330mmol) was added dropwise with stirring at 55°C for 2h. Then, the mixture was cooled to 25°C and 1% sodium bicarbonate (150mL) was added and stirred for 10min. The organic layer was successively washed with 0.5N hydrochloric acid solution, 1% sodium bicarbonate and water. The organic phase was concentrated and dissolved in DMSO (300mL) at 45°C followed by adding sodium hydroxide (68g/100g water). The basic mixture was stirred at 55°C for 8h. The obtained mixture was treated as described above, yielding the free base (S)-6

References:

Chen, Xiang;Liu, Zhi-Qiang;Lin, Chao-Ping;Zheng, Yu-Guo [Bioorganic Chemistry,2016,vol. 65,p. 82 - 89]

161005-84-1 Synthesis