Benzenamine, 4-[(4-phenyl-1-piperazinyl)methyl]- synthesis
- Product Name:Benzenamine, 4-[(4-phenyl-1-piperazinyl)methyl]-
- CAS Number:40224-23-5
- Molecular formula:C17H21N3
- Molecular Weight:267.37
![Piperazine,1-[(4-nitrophenyl)methyl]-4-phenyl-](/CAS/20180601/GIF/40224-22-4.gif)
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Yield: 85%
Reaction Conditions:
with iron;ammonium chloride in ethanol;water at 70 - 80; for 4 h;
Steps:
4-[(4-phenylpiperazin-1-yl)methyl]aniline (29)
1-(4-Nitrobenzyl)-4-phenylpiperazine thus obtained (1.30 g,4.37 mmol) was dissolved in EtOH (18 mL) and water (18 mL), and the solution was heated to 70°C. Fe powder (732 mg, 13.1 mmol) and NH4Cl (1.17 g, 21.9 mmol) were added, and the mixture was stirred at 80°C for 4 hours. After cooling to room temperature, the mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo. The resulting residue was basified with saturated aqueous NaHCO3, and extracted with EtOAc (x3). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo to afford the title compound (1.00 g, 85%). 1H NMR (300 MHz, DMSO-d6) δ 2.45 (t, J = 4.4 Hz, 4H), 3.09 (t, J = 4.4 Hz, 4H), 3.31 (s, 2H), 4.98 (s,2H), 6.51 (d, J = 8.0 Hz, 2H), 6.75(t, J = 7.3 Hz, 1H), 6.90 (d, J = 8.8 Hz, 2H), 6.95 (d, J = 8.0 Hz, 2H), 7.16-7.22 (m, 2H).
References:
Nakano, Hirofumi;Hasegawa, Tsukasa;Imamura, Riyo;Saito, Nae;Kojima, Hirotatsu;Okabe, Takayoshi;Nagano, Tetsuo [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 9,p. 2370 - 2374] Location in patent:supporting information
92-54-6
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100-11-8
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40224-22-4
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40224-23-5
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92-54-6
422 suppliers
$13.00/5g
40224-23-5
4 suppliers
inquiry
100-11-8
14 suppliers
$13.00/5g
40224-23-5
4 suppliers
inquiry