Basic information Safety Supplier Related

(RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol

Basic information Safety Supplier Related

(RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol Basic information

Product Name:
(RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol
Synonyms:
  • 1-[3-(Methylamino)-1-(2-thienyl)propyl]-2-naphthalenol
  • 1-(3-(Methylamino)-1-(thiophen-2-yl)propyl)naphthalen-2-ol
  • Duloxetine 2-Naphthalenol Impurity
  • Duloxetine Impurity 10(Duloxetine USP RC H)
  • (RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol
  • Duloxetine USP Related Compound H
  • Duloxetine 2-Naphthalenol Imp
  • Duloxetine EP Impurity E (USP RC E)
CAS:
1346599-09-4
MF:
C18H19NOS
MW:
297.41
Mol File:
1346599-09-4.mol
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(RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol Chemical Properties

Melting point:
132-136°C
Boiling point:
492.8±45.0 °C(Predicted)
Density 
1.189
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
9.08±0.50(Predicted)
form 
Solid
color 
White to Off-White
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(RS)-1-[3-(MethylaMino)-1-(2-thienyl)propyl]-2-naphthalenol Usage And Synthesis

Uses

An impurity of the antidepressant Duloxetine (D721000). Duloxetine Impurity 10.

Synthesis

(1) add 10g of duloxetine, 50mL of ethyl acetate and 8mL of hydrogen chloride solution of ethyl acetate with a concentration of 12.6% to a 100mL three-necked flask at room temperature, stir for 10min, raise the temperature to 35C and hold it for 24h, and then lower the temperature to 20C, and filter it to obtain the filter cake M and the filtrate N at that temperature;

(2) the filtrate N obtained in step (1) was distilled under reduced pressure at 40 and vacuum degree P=-0.099MPa until no fraction was distilled out, and the residual liquid F was obtained as 4.70g, and the residual liquid F was added into 30mL of ethyl acetate, and dialyzed under stirring at 25 for 24h, and filtered to obtain the filtrate cake X of about 4.2g and the filtrate Y, and the filtrate cake X was added into 20mL methanol and stirred to be dialyzed under 20 for 12h, and obtained the filtrate cake S of about 4.2g and filtrate Y, and then added the filter cake S of about 4.2g and filtered under stirring at 20 for 12h. The filter cake X was added to 20 mL of methanol and stirred to crystallize at 20C for 12h, obtaining the filter cake S of about 3.5g and the filtrate T;

(3) the filtrate T in step (2) was distilled under reduced pressure at 40 , vacuum P = -0.099MPa until no fraction was distilled, and the residual liquid W was obtained, and the residual liquid W was added to 20mL of ethyl acetate, and then precipitated under stirring at 0 for 12h, and then filtered, and the filtrate obtained was distilled under reduced pressure at 50 , and the residual ethyl acetate was evaporated to the exhaustion, and the residual liquid was obtained as about 2g, i.e., the ( RS)-1-[3-methylamino-1-(2-thienyl)]propyl]-2-naphthol.

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