1,3-Dibromobenzene → 1-(3-Bromophenyl)-4-methylpiperazine

HRID 2168160Notes

Reaction equation

HRID 2168160 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1>COC(C)(C)C>[Br:15][C:11]1[CH:10]=[C:9]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 79271,3-DibromobenzeneHCID 531671-Methylpiperazine

Product 1

HCID 534153291-(3-Bromophenyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

1-Methyl-piperazine (1 ml, 8.99 mmol) and 1,3-dibromo-benzene (3 ml, 24.82 mmol) are heated to 200° C. in a sealed tube under microwave irradiation for 300 min (150 W, 9 bar). The residue is diluted with tert-butyl methyl ether (50 ml) and extracted with 1M HCl. The aqueous layer is neutralized with sodium bicarbonate, and extracted with ethyl acetate (150 ml). The organic layer is separated and dried over MgSO4. The drying agent is filtered and the solvent is removed in vacuum; yield: 700 mg 1-(3-bromo-phenyl)-4-methyl-piperazine; HPLC/MS: 1.24 min, [M+H]=255.

Workup

  1. extractionextracted with 1M HCl
  2. extractionextracted with ethyl acetate (150 ml)
  3. customThe organic layer is separated
  4. dry with materialdried over MgSO4
  5. filtrationThe drying agent is filtered
  6. customthe solvent is removed in vacuum
  7. custom1.24 min, [M+H]=255

Sources & evidence

ORD record
ord-3348b72d8d484cce8e211e55b78f59cb
Source dataset
uspto-grants-2015_06
Patent number
US09045493B2

Reaction notes

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