Tetrahydrofuran → (S)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-piperazine

HRID 344021Notes

Reaction equation

HRID 344021 reaction equation
O1CCCC1.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][C@@H:16]2[NH:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]2=O)=[CH:7]1.[OH-].[Na+]>O>[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][C@@H:16]2[NH:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:17]2)=[CH:7]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9905691(S)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-2-oxo-piperazine

Product 1

HCID 53963367(S)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Combine lithiium aluminumhydride (100 mmol) and tetrahydrofuran (75 ml). Add (S)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-2-oxo-piperazine (25 mmol) portionwise. Heat to reflux. After 24 hours, cool to ambient temperature. Carefully add water (3.8 mL), 15% aqueous sodium hydroxide solution (3.8 mL), and water (10.5 mL). Stir vigourously for 1 hour. Filter, rinse the filter cake repeatedly with tetrahydrofuran. Concentrate the filtrate in vacuo to obtain a residue. Chromatograph the residue to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. filtrationFilter
  3. washrinse the filter cake repeatedly with tetrahydrofuran
  4. concentrationConcentrate the filtrate in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-b173553cc52246178cdd6b8cc35a4b51
Source dataset
uspto-grants-1999_01
Patent number
US05864045

Reaction notes

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