147199-40-4

Basic information

• Product Name: (S)-N-Didemethyl Dapoxetine
• Synonyms: (S)-N-Didemethyl Dapoxetine ;N-Didemethyl Dapoxetine Hydrochloride;(S)-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine hydrochloride
• CAS NO: 147199-40-4
• Molecular Formula: C₁₉H₁₉NO
• Molecular Weight: 277.36026
• Product Categories: Amines;Aromatics;Chiral Reagents;Metabolites & Impurities
• Mol File: 147199-40-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 462.6±38.0 °C(Predicted)
• Appearance: /
• Density: 1.128±0.06 g/cm3(Predicted)
• PKA: 8.67±0.10(Predicted)
• CAS DataBase Reference: (S)-N-Didemethyl Dapoxetine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Didemethyl Dapoxetine(147199-40-4)
• EPA Substance Registry System: (S)-N-Didemethyl Dapoxetine(147199-40-4)

Safety Data

• Hazardous Substances Data: 147199-40-4(Hazardous Substances Data)

Upstream product

• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 41198-42-9 3-(naphthalen-1-yloxy)-1-phenylpropan-1-one 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 14593-04-5 3-amino-3-phenyl-1-propanol 
• 100-52-7 benzaldehyde 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 119357-34-5 1-phenyl-3-(naphthyl-1-oxy)propylamine 

Downstream Products

• 119356-77-3 dapoxetine 
• 1071929-03-7 Dapoxetine hydrochloride 
• 1404234-03-2 (S)-tert-butyl(3-(naphthalen-1-yloxy)-1-phenylpropyl)carbamate 

Relevant articles and documents

Synthesis method of dapoxetine impurities

The invention provides a synthesis method of dapoxetine impurities, which comprises the following synthesis steps of: reacting (S)-3-amino-3-phenyl propanol with Boc anhydride to obtain a compound B; reducing the compound B under the action of a reducing agent to obtain a dapoxetine impurity 1; reacting the impurity 1 with 1-fluoronaphthalene under the action of alkali to obtain an impurity 2; and reacting the impurity 2 with chloroformate to obtain an impurity 3. According to the synthesis method of the dapoxetine impurities, the three dapoxetine impurities can be obtained in sequence, the starting raw materials are wide in source, the cost is low, the synthesis steps are short, all the steps are conventional experiment operation, special reagents or toxic reagents do not need to be used, and the prepared dapoxetine impurity products are high in purity and do not need tedious purification operation. The synthesized three impurities are applied to dapoxetine hydrochloride quality control, are helpful for perfecting the quality standard of dapoxetine hydrochloride, and have important meanings for improving the quality of dapoxetine hydrochloride raw material medicines and preparations thereof and the medication safety.

Synthetic method of dapoxetine intermediate and intermediate synthesized with method

The invention discloses a synthetic method of a dapoxetine intermediate and the intermediate synthesized with the method. The method comprises steps as follows: a compound (4) is prepared from a compound (2) and a compound (3) as starting raw materials th

Preparation method of dapoxetine hydrochloride impurities

The invention discloses a preparation method of three impurities with similar structures for dapoxetine hydrochloride: (S)-3-(naphthalene-1-oxo)-1-phenylpropy-1-amine (compound II), (S)-N-methyl-3-(naphthalene-1-oxo)-1-phenylpropy-1-amine (compound III) and (S)-N,N-dimethyl-3-(naphthalene-2-oxo)-1-phenylpropy-1-amine (compound IV). The preparation method comprises the following steps: taking (S)-3-amino-3-phenylpropy-1-ol (VII) as a starting raw material; carrying out a multiple-step reaction such as amino protection, hydroxyl activation, substitution and amino deprotection to respectively obtain a compound II, a compound III and a compound IV as impurities of the dapoxetine hydrochloride. According to a preparation route, the starting raw materials are easy to obtain; reaction conditionsare mild and the selectivity is high; a sample with higher purity (98 percent or above) can be obtained according to a conventional post treatment method, can be used as a reference substance of the compound II, the compound III and the compound IV that are impurities of the dapoxetine hydrochloride and is used for quality control over synthesis research of the dapoxetine hydrochloride.