Tetrahydrofuran → HCID 131716332, compound

HRID 1164976Notes

Reaction equation

HRID 1164976 reaction equation
O1CCCC1.[ClH:6].[CH2:7]([N:9]1[CH:14]([CH2:15][O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:13][N:12]([C:21]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)[C:11](=O)[CH2:10]1)[CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOC(C)=O.O>[ClH:6].[ClH:6].[CH2:7]([N:9]1[CH2:10][CH2:11][N:12]([C:21]2[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:25][CH:26]=2)[CH2:13][CH:14]1[CH2:15][O:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH3:8]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19863429HCID 19863429, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131716332HCID 131716332, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 5 mL of tetrahydrofuran under a nitrogen atmosphere add 2.6 g (6.8 mmol) of N-[4-[4-ethyl-5-[(2-methylpropoxy)methyl]-2-oxopiperazin-1-yl]phenyl]methanesulfonamide hydrochloride and 0.51 (13 mmol) of lithium aluminum hydride. When the additions are complete stir the reaction at reflux. Monitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1). Upon completion of the reaction cool to room temperature and add 0.5 mL of H2O, 0.5 mL of 2N NaOH, 1.5 mL of H2O, and 50 mL of EtOAc. Remove the precipitate by suction filtration through celite and remove the solvent in vacuo. Chromatograph the residue on silica gel with CH2Cl2 :MeOH. Combine the product fractions and remove the solvent in vacuo. Dissolve the residue in methanolic HCl and remove the solvent in vacuo. Recrystallize the material from isopropanol to afford the title compound.

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1)
  4. customRemove the precipitate
  5. filtrationby suction filtration through celite
  6. customremove the solvent in vacuo
  7. customremove the solvent in vacuo
  8. dissolutionDissolve the residue in methanolic HCl
  9. customremove the solvent in vacuo
  10. customRecrystallize the material from isopropanol

Sources & evidence

ORD record
ord-2b688540cf8e4b3d952b2ada55b82f00
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

Loading…