Benzyl Bromide → HCID 70246716, compound

HRID 1978382Notes

Reaction equation

HRID 1978382 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([CH3:14])[NH:11][CH2:10][C@@H:9]1[CH3:15])=[O:7])([CH3:4])(C)C.[CH2:16](N(CC)CC)[CH3:17].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][C@@H:9]1[CH3:15])=[O:7])[CH2:4][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 11745988(2S,5R)-1-Boc-2,5-dimethylpiperazine

Product 1

HCID 70246716HCID 70246716, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (40 ml) solution of 4.5 g (21.0 mmol.) of trans-1-tert-butoxycarbonyl-2,5-dimethyl piperazine and 5.9 ml (42.3 mmol.) of triethylamine was added, at room temperature, 3.2 ml (26.9 mmol.) of benzyl bromide. The mixture was heated for 24 hours under reflux. The solvent was distilled off under reduced pressure. To the residue was added water. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography (ethyl acetate/hexane 10%) to give the object compound as a pale yellow oily product. The yield was 5.17 g (81%).

Workup

  1. temperatureThe mixture was heated for 24 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water
  5. extractionThe mixture was subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous saline solution, which
  7. dry with materialwas dried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by means of a column chromatography (ethyl acetate/hexane 10%)
  10. customto give the object compound as a pale yellow oily product

Sources & evidence

ORD record
ord-6c3773c9bc4147aa8332e686254d96b6
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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