ChemicalBook CAS DataBase List 3-(4-METHYL-PIPERAZIN-1-YLMETHYL)-ANILINE

3-(4-METHYL-PIPERAZIN-1-YLMETHYL)-ANILINE synthesis

7synthesis methods

Product Name:3-(4-METHYL-PIPERAZIN-1-YLMETHYL)-ANILINE
CAS Number:198281-55-9
Molecular formula:C12H19N3
Molecular Weight:205.3

198281-54-8
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3-(4-METHYL-PIPERAZIN-1-YLMETHYL)-ANILINE

198281-55-9
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Yield:198281-55-9 95%

Reaction Conditions:

with hydrogen

Steps:

23.A

A. 3-(4-Methyl-piperazin-1-ylmethyl)-phenylamine m-Nitrobenzyl bromide (500 mg, 2.31 mmol) was added to a mixture of 1-methylpiperazine (277 mg, 2.77 mmol) and potassium carbonate (414 g, 3.0 mmol) in 5 mL of DMF. The mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, the mixture was extracted into ethyl acetate (EtOAc), washed with water, brine and then dried with sodium sulfate (Na₂SO₄). Removal of the solvent and chromatography on silica, eluding with EtOAc/CH₃OH/NH₄OH (10:1:0.1, v/v), gave 510 mg of 1-methyl-4-(3-nitro-benzyl)-piperazine, which was converted to the title compound under normal hydrogenation conditions. The titled compound was obtained as a yellow solid (450 mg, 95%). ¹H NMR (400 MHz, CDCl₃) δ (ppm): 7.02 (t, J=7.6 Hz, 1H), 6.62 (s, 1H), 6.60 (d, J=7.6 Hz, 1H), 6.54 (d, J=7.6 Hz, 1H), 3.43 (s, 2H), 2.76 (br, 4H), 2.65 (br, 4H), 2.82 (m, 4H), 2.46 (s, 3H).

References:

US2007/60577,2007,A1 Location in patent:Page/Page column 42