3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one Chemical Properties

Boiling point:

368.7±25.0 °C(Predicted)

Density 

1.072

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.78±0.28(Predicted)

Appearance

Colorless to light yellow Viscous liquid

InChI

InChI=1S/C15H17NO/c1-16(2)11-10-15(17)14-9-5-7-12-6-3-4-8-13(12)14/h3-9H,10-11H2,1-2H3

InChIKey

CXDXSNWZXJVDMC-UHFFFAOYSA-N

SMILES

C(C1=C2C(C=CC=C2)=CC=C1)(=O)CCN(C)C

3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one Usage And Synthesis

Uses

3-(Dimethylamino)-1-(1-Naphthalenyl)-1-Propanone is a compound related to TMC207 which is used in the treatment of drug-resistant tuberculosis, and was studied for its anti-tubercular activity.

Synthesis

1-Acetylnaphthalene (8 g, 0.047 mol), paraformaldehyde (2 g, 0.065 mol) and dimethylamine hydrochloride (5.3 g, 0.065 mol) were dissolved in ethanol (15 mL), followed by the addition of 0.6 mL of concentrated hydrochloric acid. The reaction mixture was heated to reflux for 12 hours, after which it was cooled to room temperature and refrigerated at -20 °C overnight. A white solid precipitated from the reaction mixture, which was separated by filtration and washed with ethanol. The resulting white solid was dissolved in water and 50% aqueous sodium carbonate solution (5.8 g, 0.54 mol) was slowly added. After stirring for 10-15 min, the aqueous phase was extracted with ethyl acetate (20 mL x 3), the organic layers were combined, washed sequentially with water (15 mL x 2) and saturated saline (15 mL x 2), and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain the target compound 3-dimethylamino-1-(naphthalen-5-yl)acetone as a colorless oil (8 g, 70% yield).

References

[1] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 790 - 792
[2] Patent: EP2371819, 2011, A1. Location in patent: Page/Page column 7
[3] Patent: EP2573067, 2013, A1. Location in patent: Paragraph 0065; 0066
[4] Patent: TW2016/4185, 2016, A. Location in patent: Paragraph 0342; 0343
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 10, p. 1019 - 1024

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