1-Methylpiperazine → HCID 86701064, compound

HRID 589458Notes

Reaction equation

HRID 589458 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.CC(C)([O-])C.[K+].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[Br:9][C:4]1[CH:3]=[C:2]([N:20]2[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 1370031,3-Dibromo-5-fluorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86701064HCID 86701064, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 1,3-dibromo-5-fluorobenzene (LXI) (2.0 g, 7.88 mmol) in toluene (20 ml) was added potassium t-butoxide (2.65 g, 23.6 mmol) and 1-methylpiperazine (1.75 mL, 15.8 mmol). The reaction was heated at 105° C. overnight. The toluene was removed under vacuum and the residue was dissolved in water and extracted with EtOAc. The organic phase was separated, washed with brine, dried over MgSO4 and concentrated to dryness. The crude product was purified on a silica gel column (1:99 MeOH:CHCl3→7:93 MeOH:CHCl3) to produce 1-(3-bromo-5-fluorophenyl)-4-methylpiperazine (LXII) as an orange oil (800 mg, 2.93 mmol, 37.2% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 2.20 (s, 3H), 2.39 (t, J=5 Hz, 4H), 3.33 (t, J=5 Hz, 4H), 6.74-6.81 (m, 2H), 6.91 (s, 1H); ESIMS found for C11H4BrFN2 m/z 273 (M+H).

Workup

  1. customThe toluene was removed under vacuum
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified on a silica gel column (1:99 MeOH:CHCl3→7:93 MeOH:CHCl3)

Sources & evidence

ORD record
ord-1d148c395cfb4749a82eefd5d3526264
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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