4'-PIPERAZINOACETOPHENONE Chemical Properties

Melting point:

107-110 °C(lit.)

Boiling point:

342.77°C (rough estimate)

Density 

1.0565 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

2-8°C

solubility 

Benzene (Slightly, Heated), Chloroform (Slightly), DMSO (Slightly, Heated)

pka

8.80±0.10(Predicted)

form 

Powder or Chunks

color 

Yellow

CAS DataBase Reference

51639-48-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-34-21/22

Safety Statements 

26-37/39

RIDADR 

3259

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4'-PIPERAZINOACETOPHENONE Usage And Synthesis

Chemical Properties

yellow powder or chunks

Uses

1-[4-(1-Piperazinyl)phenyl]ethanone is a useful building block for organic synthesis.

Synthesis

1. Potassium carbonate (2.99 g, 21.6 mmol) was placed in a round-bottomed flask and dried under vacuum with a hot air gun. 2. Tetrabutylammonium bromide (0.045 g, 0.14 mmol) and piperazine (1.54 g, 17.9 mmol) dissolved in anhydrous dimethyl sulfoxide (5 mL) were added sequentially. 3. The reaction mixture was stirred at 80 °C, followed by the addition of 4-fluoroacetophenone (2 g, 14.4 mmol) and the reaction was refluxed for 15 h at the same temperature. 4. After completion of the reaction, the mixture was cooled to room temperature, diluted with water and the solid was collected by filtration. 5. The filtrate was acidified with dilute hydrochloric acid and subsequently extracted with ethyl acetate. 6. The aqueous layer was alkalized with sodium hydroxide and extracted with chloroform. 7. The chloroform layers were combined, dried over anhydrous sodium sulfate and concentrated to give the light yellow solid product 4'-piperazineacetophenone (2.23 g, 75.25% yield, melting point 109°C). 8. The product was analyzed by 1H NMR. 8. The product was characterized by 1H NMR (200 MHz, CDCl3): δ 1.91 (s, 1H), 2.52 (s, 3H), 2.98-3.05 (m, 4H), 3.28-3.35 (m, 4H), 6.87 (d, J = 8.8 Hz, 2H), 7.87 (d, J = 8.8 Hz, 2H).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5507 - 5520
[2] Patent: WO2014/132267, 2014, A1. Location in patent: Page/Page column 33
[3] Patent: WO2005/7637, 2005, A1. Location in patent: Page 7-8

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