Sodium Hydroxide → 6-Ethyl-3-oxo-n-(5-phenyl-2-pyrazinyl)spiro[isobenzofuran-1-(3h),4'-piperidine]-1'-carboxamide

HRID 392808Notes

Reaction equation

HRID 392808 reaction equation
Cl.[CH2:2]([C:4]1[CH:17]=[C:16]2[C:7]([C:8](=[O:18])[O:9][C:10]32[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[CH:6][CH:5]=1)[CH3:3].[C:19]1([C:25]2[N:26]=[CH:27][C:28]([NH:31][C:32](=O)[O:33]C3C=CC=CC=3)=[N:29][CH:30]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>CS(C)=O>[CH2:2]([C:4]1[CH:17]=[C:16]2[C:7]([C:8](=[O:18])[O:9][C:10]32[CH2:11][CH2:12][N:13]([C:32]([NH:31][C:28]2[CH:27]=[N:26][C:25]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:30][N:29]=2)=[O:33])[CH2:14][CH2:15]3)=[CH:6][CH:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 9879110Phenyl 5-phenylpyrazin-2-ylcarbamateHCID 226607156-ethylspiro[isobenzofuran-1(3H),4'-piperidine]-3-one hydrochloride

Product 1

HCID 226607536-Ethyl-3-oxo-n-(5-phenyl-2-pyrazinyl)spiro[isobenzofuran-1-(3h),4'-piperidine]-1'-carboxamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 6-ethylspiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (53 mg) and phenyl N-(5-phenyl-2-pyrazinyl)carbamate (58 mg) in dimethyl sulfoxide (1 mL) was added 10 M sodium hydroxide aqueous solution (0.02 mL). The mixture was vigorously stirred for 5 minutes followed by partition between water and ethyl acetate. The organic layer was separated and then washed with saturated saline solution and then dried over anhydrous Na2SO4 The concentration of the organic solvent left a residue, which was subjected to the crystallization from ethyl acetate to give the subject compound (46 mg) as crystals (melting point 176-178° C.).

Workup

  1. customby partition between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated saline solution
  4. dry with materialdried over anhydrous Na2SO4 The concentration of the organic solvent
  5. waitleft a residue, which
  6. customwas subjected to the crystallization from ethyl acetate

Sources & evidence

ORD record
ord-89b94acaf0c34eb191ef3e624fd24a95
Source dataset
uspto-grants-2004_10
Patent number
US06803372B2

Reaction notes

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