Sodium Hydroxide → 1-[2-Amino-4-(4-methyl-piperazin-1-yl)-phenyl]-ethanone

To a solution of 1-[2-hydroxy-4-(4-methyl-piperazin-1-yl)-phenyl]-ethanone (5.22 g, 22.2 mmol) in DMA (50 mL) NaOH (2.67 g, 66.6 mmol) was added. The mixture was stirred at room temperature for 1 h, after which time 11.1 g (66.7 mmol) of 2-bromo-2-methylpropanamide was added and the mixture was stirred at room temperature overnight. 8.01 g (200 mmol) of NaOH was added and the resulting mixture was stirred at 100° C. for 2 h, then 50 mL of water was added and the mixture was stirred at 100° C. for 1 h. After cooling to room temperature, the mixture was concentrated and then diluted with DCM and washed with water, dried over sodium sulfate and concentrated. The crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 95/5) to afford 1.51 g of the title compound (30% yield).

1. stirringthe mixture was stirred at room temperature overnight
2. stirringthe resulting mixture was stirred at 100° C. for 2 h
3. stirringthe mixture was stirred at 100° C. for 1 h
4. temperatureAfter cooling to room temperature
5. concentrationthe mixture was concentrated
6. additiondiluted with DCM
7. washwashed with water
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customThe crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 95/5)

ORD record

ord-78abcd34a3204be38eee0086ded2fbd0

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614220B2