(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine Chemical Properties

Melting point:

78-80°C

Boiling point:

290°C

Density 

1.111

Flash point:

129°C

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

13.74±0.20(Predicted)

form 

Solid

color 

White

InChI

InChI=1/C9H15NOS/c1-10(2)6-5-8(11)9-4-3-7-12-9/h3-4,7-8,11H,5-6H2,1-2H3/t8-/s3

InChIKey

XWCNSHMHUZCRLN-SBYBRXNCNA-N

SMILES

C(N(C)C)C[C@H](O)C1SC=CC=1 |&1:5,r|

CAS DataBase Reference

132335-44-5(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29349990

(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine Usage And Synthesis

Chemical Properties

White Solid

Uses

A Duloxetine intermediate.

Synthesis

General procedure for the synthesis of (S)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine from N/A (Example 23): under argon protection, (R,R)-Cl2((R)-hexylBINAP)((R)-DAIPEN) (30.5 mg, 0.025 mmol), 2-propanol (100 ml), 1.0 M tert-butyl potassium oxychloride solution of 2-propanol (7.5 ml, 7.5 mmol) and 3-(N,N-dimethylamino)-1-(2-thienyl)-1-propanone (22.9 g, 0.125 mol) were added sequentially to a glass autoclave. After the reaction system was degassed several times and replaced with argon, hydrogen was introduced to a predetermined pressure to start the reaction. After stirring the reaction at 28°C for 6 hours, the reaction system was returned to normal temperature and pressure. The reaction solution was concentrated, heptane was added and the precipitated solid was filtered. The resulting solid was dried under reduced pressure to afford (S)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine 18.5 g in 80.0% yield. The optical purity of the product was determined by chiral column HPLC, and the result showed that the optical purity was 99% ee. Note: (R)-DAIPEN is (R)-1-isopropyl-2,2-bis(p-methoxyphenyl)ethylenediamine, and xylBINAP is 2,2'-bis(bis-3,5-dimethylphosphinodiphenyl)-1,1'-binaphthyl.

References

[1] Patent: EP1506965, 2005, A1. Location in patent: Page/Page column 35
[2] Angewandte Chemie (International ed. in English), 2004, vol. 43, # 21, p. 2816 - 2819
[3] Chemistry - A European Journal, 2011, vol. 17, # 28, p. 7760 - 7763
[4] Patent: US8426178, 2013, B2. Location in patent: Page/Page column
[5] Chemical Communications, 2015, vol. 51, # 61, p. 12328 - 12331

(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine(132335-44-5)Related Product Information

• Dimethyl disulfide
• ETHANE
• 3-Dimethylaminopropylamine
• Diisopropylamine
• Dimethyl sulfate
• Dimethyl ether
• Dimethyl carbonate
• Isopropylamine
• Tetrahydrothiophene
• Dimethyl fumarate
• 1-Propanol
• Cephalothin sodium
• Dacthal
• N,N-Dimethylformamide
• Dimethyl sulfoxide
• D/L-AMPHETAMINE HYDROCHLORIDE
• 3-(Dimethylamino)-1-(2-thienyl)-1-propanol
• (-)-2-[METHYLAMINO]-1-PHENYLPROPANE