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ChemicalBook CAS DataBase List 2-METHYL-4-(4-METHYLPIPERAZIN-1-YL)ANILINE
16154-71-5

2-METHYL-4-(4-METHYLPIPERAZIN-1-YL)ANILINE synthesis

4synthesis methods
-

Yield:16154-71-5 800 mg

Reaction Conditions:

Stage #1: 1-methyl-4-(3-methyl-4-nitrophenyl)piperazinewith palladium 10% on activated carbon in ethanol at 20; for 0.25 h;Inert atmosphere;
Stage #2: with ammsnium formate in ethanol; for 0.0333333 h;Inert atmosphere;

Steps:

2 Step 2: 2-Methyl-4-(4-methylpiperazin- 1 -yl)aniline

To a solution of l-methyl-4-(3-methyl-4-nitrophenyl)piperazine (1.0 g, 4.25 mmol) in ethanol (20 mL) was added catalytic amount of 10% palladium on carbon and the mixture was stirred at RT for 15 min under nitrogen atmosphere. Ammonium formate (2.6 g, 42.5 mmol) was added to the mixture and stirred for 2 min. The mixture was cooled to RT and filtered through celite. The filtrate was concentrated, dissolved in ethyl acetate and the organic solution was washed with saturated sodium bicarbonate solution followed by brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure to yield 800 mg of the desired product. NMR (400 MHz, DMSO-de) d 2.02 (s, 3H), 2.20 (s, 3H), 2.67-2.72 (m, 4H), 2.87-2.91 (m, 4H), 4.33 (br s, 2H), 6.48-6.56 (m, 2H), 6.59 (d, J = 2.4 Hz, 1H); ESI-MS ( m/z ) 206 (M+H)+.

References:

WO2020/70331,2020,A1 Location in patent:Page/Page column 70

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