Piperazine → HCID 117189321, compound

HRID 1051695Notes

Reaction equation

HRID 1051695 reaction equation
Br[C:2]1[N:3]([CH3:8])[CH:4]=[C:5]([Br:7])[N:6]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>ClCCl>[Br:7][C:5]1[N:6]=[C:2]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[N:3]([CH3:8])[CH:4]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 72048802,4-Dibromo-1-methyl-1H-imidazole

Product 1

HCID 117189321HCID 117189321, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A 20-mL resealable tube was charged with 2,4-dibromo-1-methyl-1H-imidazole (0.480 g, 2.00 mmol) and piperazine (3.4 g, 39.5 mmol), and the resulting mixture was stirred for 3 h at 130° C. The reaction mixture was cooled to room temperature, diluted with dichloromethane (20 mL), washed with water (2×10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol) to afford 1-(4-bromo-1-methyl-1H-imidazol-2-yl)piperazine (0.300 g, 61%) as a light yellow solid. MS (ESI, pos. ion) m/z 245, 247 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (2×10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol)

Sources & evidence

ORD record
ord-84f246b0c06942c0bde467371fe2082c
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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