Potassium Carbonate → 1-Acetyl-4-(3-amino-4-nitrophenyl)piperazine

HRID 349663Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[C:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:12]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (5 g, 29 mmol), 1-acetylpiperazine (29 mmol), and K2CO3 (4.0 g, 29 mmol) in DMF (20 mL) was stirred at 120° C. for 4 h. The reaction mixture was cooled to room temperature and poured into ice cold water (100 mL). The crude solid product was collected by filtration, air dried, and purified by flash chromatography (silica gel, 4×15 cm, eluted with CHCl3) to yield the product as orange crystals.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe crude solid product was collected by filtration, air
customdried
custompurified by flash chromatography (silica gel, 4×15 cm, eluted with CHCl3)

Sources & evidence

ORD record: ord-cf6b38e662d047fca0f815c59f99da37
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179912B2

Reaction notes

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