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

General procedure: These amines were required for the syntheses of 4 and 20 respectively. To a solution of 4-nitrobenzylchloride (1 mmol) in anhydrous THF (3 mL) was added 1-methylpiperazine or piperidine (1 mmol) and triethylamine (1.5 mmol, 0.21 mL). The solution was heated at 70 °C overnight. The reaction mixture was then extracted with dichloromethane and water. The organic fractions were combined, dried over anhydrous NaA mixture of 1-methyl-4-(4-nitro-benzyl)-piperazine (3.09 g, 13.1 mmol), zinc dust (4.29 g, 65.6 mmol) and ammonium chloride (2.81 g, 52.5 mmol) in methanol (100 mL) was refluxed 1h, cooled, filtered through Celite (washing with methanol) and evaporated to provide 4-(4-methyl-piperazin-1-ylmethyl)-phenylamine (2.67 g, 99percent yield) as a pale yellow, waxy solid. 1H-NMR (DMSO-d6, 500 MHz) 6.89 (d, 2H), 6.49 (d, 2H), 4.89 (s, 2H), 3.24 (s, 2H), 2.3 (br m, 8H) ppm; MS (FIA) 206.2 (M+H); HPLC (Method A) co-elutes with solvent front.11 g (2.35 g, 10 mmol) was dissolved in a methanol solvent, Under nitrogen protection, 200 mg of Pd / C was added, And then through the H2 reaction, 6h after the reaction is complete.The filtrate was collected by filtration, and concentrated to give 1.89 g of a solid. Yield 92percent.The Second Step: 4-Amino-N-[4-[(4-methylpiperazin-1-yl) methyl] phenyl]-1Hpyrazole-3-carboxamide (5): The mixture of N-methylpiperazine (4.9 mL, 44.2 mmol) and triethylamine (12 mL, 86.3 mmol) in dichloromethane (20 mL) was added dropwiseto a stirred solution of Nitro-benzyl bromide 1 (10.0 mg, 46.3 mmol) in dichloromethane (100 mL) under the ice-waterbath and was refluxed for 1 h. The reaction mixture was extractedwith chloroform (100 mL×3), washed with water andsaturated sodium chloride each time (100 mL×1). The organicphase was dried with anhydrous magnesium sulfate, filtered, evaporated under vacuum to give pale yellow solid 2. Withoutfurther purification, 2 mixed with FeO(OH)/C (catalyst 2.0 g)and 95percent ethanol (100 mL) were kept refluxing and dropwiseadded the mixture of hydrazine hydrate (25 mL) and 95percentethanol (20 mL), then filtrated when the solution was hot. Theresidue was washed with hot ethanol (30 mL×2). The solventwas distilled under vacuum to give white solid 3 (6.7 g), thenmixed with 4-nitro-1H-pyrazole-3-acid (6.3 g, 40.0 mmol), EDCI (8.4 g, 43.8 mmol) and HOBT (6.0 g, 44.4 mmol) in anhydrousDMF (100 mL), stirred for 24 h at room temperature.The reaction mixture was poured into ice water (200 mL).A large amount of yellow solid precipitation was acquired.The pure product 4 was got from recrystallizing with mixedsolvent of methanol and ethyl acetate, then the same processof hydrazine hydrate reduction was done with the catalyst ofFeO(OH)/C. The solvent was distilled under vacuum to give white solid 5 (3.5 g). Yield= 63.9percent; mp 199–201°C; IR (KBr)cm−1: 3369, 3227 (NH2), 1346 (C= C), 1456 (C= N) pyrazole, 646 (ArH); 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.1 (3H, s, –CH3), 2.3–2.5 (8H, m, –CH2–), 3.3 (2H, s, –CH2–), 4.7(1H, s, –NH2), 7.1–7.2 (3H, m, ArH), 7.7 (2H, d, J=10.5 Hz, ArH), 9.7 (1H, s, –NHCO–), 12.7 (1H, s, Pyrazole); MS m/z:315.82 (M+); Anal. Calcd for C16H22N6O: C, 61.13; H, 7.05; N, 26.73; O, 5.09. Found: C, 61.31; H, 6.84; N, 26.52.A solution of 4-(4-methylpiperazine-1-carbonyl)aniline (1.03g, 4.56 mmol) in THF (50 mL) was cooled to 0°C and LiAlH

Molecular Weight:205.30
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:205.157897619
Monoisotopic Mass:205.157897619
Topological Polar Surface Area:32.5
Heavy Atom Count:15
Complexity:179
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes