1-Methylpiperazine → 5-(4-Methylpiperazin-1-yl)-2-nitroaniline

5-Chloro-2-nitroaniline (500 g, 2.898 mol) and 1-methyl piperazine (871 g, 8.693 mol) were placed in a 2000 mL flask fitted with a condenser and purged with N2. The flask was placed in an oil bath at 100° C. and heated until the 5-chloro-2-nitroaniline was completely reacted (typically overnight) as determined by HPLC. After HPLC confirmed the disappearance of the 5-chloro-2-nitroaniline, the reaction mixture was poured directly (still warm) into 2500 mL of room temperature water with mechanical stirring. The resulting mixture was stirred until it reached room temperature and then it was filtered. The yellow solid thus obtained was added to 1000 mL of water and stirred for 30 minutes. The resulting mixture was filtered, and the resulting solid was washed with TBME (500 mL, 2×) and then was dried under vacuum for one hour using a rubber dam. The resulting solid was transferred to a drying tray and dried in a vacuum oven at 50° C. to a constant weight to yield 670 g (97.8%) of the title compound as a yellow powder.

1. customfitted with a condenser
2. custompurged with N2
3. customThe flask was placed in an oil bath at 100° C.
4. temperatureheated until the 5-chloro-2-nitroaniline
5. customwas completely reacted (typically overnight)
6. additionthe reaction mixture was poured directly (
7. customreached room temperature
8. filtrationit was filtered
9. customThe yellow solid thus obtained
10. stirringstirred for 30 minutes
11. filtrationThe resulting mixture was filtered
12. washthe resulting solid was washed with TBME (500 mL, 2×)
13. customwas dried under vacuum for one hour
14. customdried in a vacuum oven at 50° C. to a constant weight

ORD record

ord-2087d835add444f78cc4a98e71fe2030

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825132B2