N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical Properties

Melting point:

152 - 154°C

Boiling point:

434.8±40.0 °C(Predicted)

Density 

1.151

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

7.43±0.10(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C14H22N4O/c1-16-7-9-18(10-8-16)11-14(19)17(2)13-5-3-12(15)4-6-13/h3-6H,7-11,15H2,1-2H3

InChIKey

LBWNQLVDYPNHAV-UHFFFAOYSA-N

SMILES

N1(CC(N(C2=CC=C(N)C=C2)C)=O)CCN(C)CC1

Safety Information

HS Code 

2933998090

N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide Usage And Synthesis

Uses

N-(4-Aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide acts as a reagent for the preparation, angiokinase inhibitory, antitumor activity and pharmacokinectic properties of deuterated derivatives of nintedanib.

Synthesis

GENERAL STEPS: 2-Chloro-N-methyl-N-(4-nitrophenyl)acetamide (210.0 g, 0.9185 mol) was suspended in toluene (1157.56 mL) and heated to 40 °C. The mixture was then purified by aqueous solution of N-methylpiperazine (252.65 mL, 2.48 eq.). N-methylpiperazine (252.65 mL, 2.48 eq.) was added dropwise over 30 min. The reaction mixture was stirred at 55 °C for 2 hours. After cooling to room temperature, the reaction mixture was washed with water (157.23 mL) and the organic layer was diluted with isopropanol (1075.33 mL). Palladium/carbon catalyst (18.81 g) was added and hydrogenated overnight at 20 °C under 1 bar hydrogen pressure. After the reaction was complete, the catalyst was removed by filtration and the filtrate was concentrated to about 150 mL and ground with ether (120.0 mL). The crystalline product was collected by filtration, washed with ether and dried under vacuum to afford N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide 170 g (70.5% yield).

References

[1] Patent: WO2012/68441, 2012, A2. Location in patent: Page/Page column 13; 14

N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide(262368-30-9)Related Product Information

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