4-(4-Methylpiperazino)aniline Chemical Properties

Melting point:

89 °C

Boiling point:

180°C/5mmHg(lit.)

Density 

1.092±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Solid

pka

8.08±0.42(Predicted)

color 

Very Dark Gray to Black

Sensitive 

Air Sensitive

InChI

InChI=1S/C11H17N3/c1-13-6-8-14(9-7-13)11-4-2-10(12)3-5-11/h2-5H,6-9,12H2,1H3

InChIKey

MOZNZNKHRXRLLF-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(N2CCN(C)CC2)C=C1

CAS DataBase Reference

16153-81-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

3259

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

III

HS Code 

29349990

4-(4-Methylpiperazino)aniline Usage And Synthesis

Chemical Properties

Purple solid

Uses

4-(4-Methylpiperazino)aniline is a reagent in the preparation of benzyloxypyridinone derivative which has c-Met kinase inhibitor properties.

Synthesis

GENERAL METHOD: 1-methyl-4-(4-nitrophenyl)piperazine (5.53 mmol) was dissolved in methanol (15 mL) and stirred under N2 atmosphere. Pd/C (2.78 mmol) was added to this solution. Subsequently, the reaction flask was placed in H2 atmosphere (balloon) for hydrogenation reaction overnight. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth plate and the filtrate was concentrated under vacuum. The crude product was purified by silica gel column chromatography (eluent: 5% MeOH/DCM containing 1% NH3) to afford the target compound 4-(4-methyl-1-piperazinyl)aniline (3a) as a brown solid in 87% yield.

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 26, p. 8261 - 8269
[2] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 896 - 905
[3] Patent: US6569878, 2003, B1
[4] Patent: EP1215208, 2002, A2. Location in patent: Example C(70)
[5] Patent: WO2012/110773, 2012, A1. Location in patent: Page/Page column 58; 59

4-(4-Methylpiperazino)aniline(16153-81-4)Related Product Information

• 1,2-Dimethylhydrazine Dihydrochloride
• N,N-Dimethyl-1,4-phenylenediamine
• 1-BENZHYDRYLPIPERAZINE
• 4-Aminobenzotrifluoride
• Aniline
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• Dichloromethylphenylsilane
• N-Methylaniline
• 1-Methylpiperazine
• ANILINE BLACK
• N,N-Dimethylaniline
• 3,4'-DIAMINODIPHENYLMETHANE
• p-Toluidine
• Tris(hydroxymethyl)aminomethane
• 4-(4-methylpiperazin-1-yl)aniline
• Benzenamine, 4-(4-methyl-1-piperazinyl)-, monohydrochloride
• 1-METHYL-4-(4-NITROPHENYL)PIPERAZINE
• 2-(4-Methylpiperazin-1-yl)aniline