1-Methylpiperazine → 5-Bromo-2-(4-methylpiperazin-1-yl)pyridine

HRID 423410Notes

Reaction equation

HRID 423410 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 164142065-Bromo-2-(4-methylpiperazin-1-yl)pyridineYield 64.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat 2-fluoro-5-bromopyridine (2.15 g, 12.22 mmol) with 1-methyl-piperazine (3.4 mL, 30.54 mmol) in THF (10 mL) in a microwave reactor at 120° C. for 45 min. Dilute with EtOAc (60 mL), then wash with NaHCO3 (2×30 mL) and brine (20 mL). Dry with Na2SO4, filter, and concentrate to give 2.01 g (64%) of the title compound. MS/ES m/z (79Br) 256 [M+H]+.

Workup

  1. washwash with NaHCO3 (2×30 mL) and brine (20 mL)
  2. dry with materialDry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-a097969f857f4984bb2c50e7f55487dd
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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