Methyl iodide → 3-(4-Bromo-phenyl)-1-methyl-piperazine

HRID 549403Notes

Reaction equation

HRID 549403 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH2:14](N(CC)CC)C.CI.[Cl-].[NH4+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[NH:9][CH2:10][CH2:11][N:12]([CH3:14])[CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 218386862-(4-Bromophenyl)piperazine

Product 1

HCID 578992273-(4-Bromo-phenyl)-1-methyl-piperazineYield 46.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-(4-bromophenyl)piperazine (4.07 g, 16.0 mmol) and triethylamine (17 mL, 122 mmol) in acetone (50 mL) was added a solution of methyl iodide (1.4 mL, 22 mmol) in acetone (20 mL) over 50 min and the reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for 16 h. The reaction mixture was slowly treated with saturated ammonium chloride (150 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash silica gel column chromatography (heptane/ethyl acetate) gave 3-(4-bromo-phenyl)-1-methyl-piperazine (1.89 g, 46% yield). LCMS (m/z): 257.00 (M+1).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. extractionextracted with ethyl acetate (200 mL×3)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via flash silica gel column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-bc8f167e016942a4a35010e6b8e2f49a
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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