Piperazine → HCID 2947276, compound

HRID 230469Notes

Reaction equation

HRID 230469 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:2]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 10821337HCID 10821337, compound

Product 1

HCID 2947276HCID 2947276, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of N-ethyl-5-fluoro-2-nitroaniline (1.5 g, 8.12 mmol), piperazine (0.979 g, 11.37 mmol), K2CO3 (3.36 g, 24.3 mmol) in DMF (40 mL) was heated in a microwave oven for 1 min at 100 W. The reaction mixture was allowed to cool and then heated for another minute at 100 w. This procedure was repeated 5 times. The suspension was filtered and then concentrated. The crude oil was purified via flash chromatography on silica using CHCl3/MeOH/NH3 9:1:0.4% as eluent to give 1.53 g (75%) of a yellow solid. 1H NMR (CDCl3) δ 8.30 (br s, 1H), 8.08-8.04 (m, 1H), 6.25-6.20 (m, 1H), 5.88-5.86 (m, 1H), 3.39-3.28 (m, 6H), 3.03-2.97 (m, 4H), 1.37 (tr, J=7.2 Hz, 3H); 13C NMR (CDCl3) δ 156.27, 147.74, 128.96, 124.13, 104.28, 93.34, 48.22, 45.99, 37.73, 14.15; MS (posEI) m/z=250 (M+); MS (posESI) m/z=found 250.1429, calc 250.1430. Anal (C12H18N4O2) C, H, O.

Workup

  1. temperaturewas heated in a microwave oven for 1 min at 100 W
  2. temperatureto cool
  3. temperatureheated for another minute at 100 w
  4. filtrationThe suspension was filtered
  5. concentrationconcentrated
  6. customThe crude oil was purified via flash chromatography on silica

Sources & evidence

ORD record
ord-bd4c842c8fb14ca2ad0f26849440463f
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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