1-Methylpiperazine → HCID 57905936, compound

HRID 1670153Notes

Reaction equation

HRID 1670153 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>S(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)=[O:7])[CH:8]=[C:9]([I:11])[CH:10]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 57905936HCID 57905936, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-bromo-5-iodo-benzoic acid (5.0 g, 15.3 mmol) in 100 mL of thionyl chloride was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting solid was then dissolved in 100 mL of CH2Cl2. N-Methyl-piperazine (2.5 mL, 22.9 mmol) and DIPEA (5.3 mL, 30.6 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. The resulting solution was concentrated under reduced pressure and the crude material was purified by column chromatography (Isco™ 330 g) using 20% MeOH/EtOAc as eluting solvent to afford 5 g (80%) of (3-bromo-5-iodo-phenyl)-(4-methyl-piperazin-1-yl)-methanone as a white solid.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting solid was then dissolved in 100 mL of CH2Cl2
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. customthe crude material was purified by column chromatography (Isco™ 330 g)
  6. washas eluting solvent

Sources & evidence

ORD record
ord-9fd3bec479394e53b6047d45f26d316a
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

Loading…