Triethylamine → HCID 21993686, compound

HRID 1978372Notes

Reaction equation

HRID 1978372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)(=O)C>C(O)C>[C:25]1([CH2:24][CH2:23][CH2:22][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12503(3-Bromopropyl)benzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21993686HCID 21993686, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.06 g (37.9 mmol.) of 1-tert-butoxycarbonylpiperazine in ethanol (50 ml) were added, at room temperature, 8.0 ml (57.4 mmol.) of triethylamine and 7.09 g (39.7 mmol.) of 1-bromo-3-phenylpropane. The mixture was heated under reflux for 16 hours under nitrogen atmosphere. To the reaction system was added ethyl acetate. The mixture was washed with water and 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=25-50%). The solvent was distilled off under reduced pressure to give the object compound as a pale yellow liquid product. The yield was 8.69 g (75%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours under nitrogen atmosphere
  3. washThe mixture was washed with water
  4. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by means of a column chromatography (ethyl acetate/hexane=25-50%)
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f89d61aa3b5840f1b91be36a258f2ebb
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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