4-[(4-Methylpiperazin-1-yl)methyl]aniline Chemical Properties

Melting point:

97-99oC

Boiling point:

331.2±27.0 °C(Predicted)

Density 

1.085±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

7.65±0.10(Predicted)

form 

Solid

color 

Yellow

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2922390090

4-[(4-Methylpiperazin-1-yl)methyl]aniline Usage And Synthesis

Uses

4-(4-Methylpiperazin-1-ylmethyl)phenylamine is an intermediate used to prepare aminopyridopyrimidinones as tyrosine kinase inhibitors and anticancer agents. It is also used in the synthesis of piperazinyltrifluoromethylphenylquinolinylbenzonaphthyridinone derivatives with anticancer activities.

Synthesis

Step 2: Preparation of 4-(4-methylpiperazin-1-ylmethyl)aniline (F652-02) 1-Methyl-4-(4-nitrobenzyl)piperazine (F652-01, 4.67 g, 19.9 mmol), methanol (100 mL), zinc powder (6.5 g, 99.3 mmol), and ammonium chloride (4.3 g, 79.5 mmol) were added to a reaction vessel and heated and refluxed for 2 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered through diatomaceous earth. The filtrate was distilled under reduced pressure to remove the solvent to give a solid product. Diethyl ether was added to the solid and the insoluble material was removed by filtration. The filtrate was distilled to remove the solvent to give 4-(4-methylpiperazin-1-ylmethyl)aniline (F652-02, white solid, 3.16 g, 77% yield). LC/MS (Method 6): m/z (ESI, POS): 206 [M + H]+; retention time: 1.15 min. 1H-NMR (400 MHz, DMSO-d6) δ 2.12 (s, 3H), 2.29 (bs, 8H), 3.23 (s, 2H), 4.93 (s, 2H), 6.49 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.4 Hz, 2H).

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2917 - 2929
[2] Patent: WO2004/46120, 2004, A2. Location in patent: Page 173
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 15, p. 5738 - 5748
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1499 - 1518

4-[(4-Methylpiperazin-1-yl)methyl]aniline(70261-82-4)Related Product Information

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• Methylparaben
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• p-Toluidine
• Acid Blue 93
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• N,N-Dimethyl-1,4-phenylenediamine
• Methyl
• 1-(4-AMINOBENZOYL)-4-METHYLPIPERAZINE
• 2-[4-(4-NITROBENZYL)PIPERAZINO]ETHAN-1-OL
• 1-BENZYL-4-(4-NITROBENZYL)PIPERAZINE