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ChemicalBook CAS DataBase List 3-Hydroxy-N-methyl-3-phenyl-propylamine
42142-52-9

3-Hydroxy-N-methyl-3-phenyl-propylamine synthesis

12synthesis methods
3-Hydroxy-N-methyl-3-phenyl-propylamine is one of important intermediate of preparation fluoxetine Hydrochloride. Up to now, the method for preparing N-methyl-3-phenyl-3-hydroxy-propylamine is mainly divided into three kinds; the first kind of be replace (halogen with 3-, dialkylamine, amido or ethoxycarbonyl) Propiophenone be starting raw material, earlier after reduction, the 1-phenylpropyl alcohol that 3-is replaced is converted into 3-Hydroxy-N-methyl-3-phenyl-propylamine again; Second kind and being: the different azoles alkane of 2-methyl-5-phenyl is carried out reductive ring open makes target compound; The third be: with getting the 1-phenylpropyl alcohol that 3-replaces behind epoxy styrene and the derivative reductive ring open thereof, be translated into target compound earlier.
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Yield:42142-52-9 90%

Reaction Conditions:

with sodium tetrahydroborate in methanol at 20; for 1 h;

Steps:

1
The 2a (0.5mmol) was dissolved in 0.5mL of methanol,At room temperature was slowly added NaBH 4 (2.0mmol),Mixture was stirred at room temperature 1h.Added 2mL saturated NH 4Cl solution.The solvent was removed by distillation under reduced pressure.The residue was added 5mLNaOH (1N),With 5mLCH 2Cl 2 and extracted four times.The organic phase was collected and dried over anhydrous sodium sulfate,And concentrated to give the crude product.The crude product after column chromatography product 2b.Yield: 90%.

References:

YUFEI;YU, FEI CN103992236, 2016, B Location in patent:Paragraph 0051;0054; 0055

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