| Identification | Back Directory | [Name]
4-[(4-Methylpiperazin-1-yl)methyl]aniline | [CAS]
70261-82-4 | [Synonyms]
FN1501
AKOS BB-8955
1-(4-Aminobenzyl)-4-methylpiperazine
1-methyl-4-(4-aminobenzyl)piperazine
4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-ANILINE
4-[(4-methyl-1-piperazinyl)methyl]aniline
4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-PHENYLAMINE
4-((4-methylpiperazin-1-yl)methyl)benzenamine
4-(4-Methylpiperazin-1-ylmethyl)phenylamine95%
4-[(4-Methyl-1-piperazinyl)methyl]-benzenamine
4-(4-METHYLPIPERAZIN-1-YLMETHYL)PHENYLAMINE 95%
Benzenamine, 4-[(4-methyl-1-piperazinyl)methyl]- | [EINECS(EC#)]
200-158-5 | [Molecular Formula]
C12H19N3 | [MDL Number]
MFCD03725418 | [MOL File]
70261-82-4.mol | [Molecular Weight]
205.3 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
7.65±0.10(Predicted) | [color ]
Yellow |
| Hazard Information | Back Directory | [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 |
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