Water → 4-Fluoro-5-(4-methylpiperazin-1-yl)-2-nitroaniline

HRID 2274412Notes

Reaction equation

C(=O)(O)[O-].[Na+].[CH3:6][N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[F:14][C:15]1C(F)=[CH:20][C:18]([NH2:19])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.O>CN(C=O)C>[F:14][C:15]1[C:11]([N:10]2[CH2:9][CH2:8][N:7]([CH3:6])[CH2:13][CH2:12]2)=[CH:20][C:18]([NH2:19])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

36.2 g of sodium bicarbonate and 28.7 mL of N-methylhomopiperazine are added to a solution of 15 g of 4,5-difluoro-2-nitroaniline in 120 mL of anhydrous DMF. The reaction medium is heated to 80° C. using an oil bath for 2H30. The reaction medium is cooled to ambient temperature, then poured into 500 mL of water. The mixture is cooled using an ice bath and stirred, and precipitation occurs. The precipitate is filtered through sintered glass. The yellow solid is rinsed with water. The solid is dried in an oven at 40° C. 21.2 g of 4-fluoro-5-(4-methylpiperazin-1-yl)-2-nitrophenylamine are obtained in the form of a yellow solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 2.22 (s, 3H); 2.45 (m, 4H); 3.17 (m, 4H); 6.42 (d, J=8.0 Hz, 1H); 7.34 (broad s, 2H); 7.63 (d, J=14.5 Hz, 1H). EI mass spectrum: m/z=254: M+. (base peak)—m/z=239: (M−CH3)+—m/z=234: (M−HF)+.−m/z=183: (M−C4H9N)+—m/z=70: C4H8N+—m/z=43: C2H5N+.

Workup

temperatureThe reaction medium is cooled to ambient temperature
temperatureThe mixture is cooled
customprecipitation
filtrationThe precipitate is filtered through sintered glass
washThe yellow solid is rinsed with water
customThe solid is dried in an oven at 40° C

Sources & evidence

ORD record: ord-2ca70e300b6c4fed9466dabaa45dcec3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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