Triethylamine → HCID 67334316, compound

HRID 1670604Notes

Reaction equation

HRID 1670604 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Br:9][C:10]1[CH:11]=[CH:12][C:13](F)=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1.C(N(CC)CC)C>C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([NH:1][N:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813491-Amino-4-methylpiperazineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 67334316HCID 67334316, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Heat a mixture of 1-amino-4-methyl piperazine (0.217 mol, 25.0 g), 5-bromo-2-fluoronitrobenzene (0.239 mol, 52.6 g) and triethylamine (0.46 mol, 46 g) in ethyl acetate (900 mL) to reflux for 16 h. Cool the reaction mixture to room temperature, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate. Purify on a silica gel column using 5% methanol in dichloromethane as eluent to give the title compound (43.2 g, 63%). ES-MS m/z 315 [M+1]+.

Workup

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. washwash with water and brine
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on a silica gel column

Sources & evidence

ORD record
ord-adb7248022c14ccdae4ce44b5d4fd6fd
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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