Sodium Hydroxide → N-(2-benzothiazolyl)-1-methylsulfonylspiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 2298955Notes

Reaction equation

HRID 2298955 reaction equation
[OH-].[Na+].Cl.[CH3:4][S:5]([N:8]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:9]1)(=[O:7])=[O:6].[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[NH:31][C:32](=O)[O:33]C1C=CC=CC=1>CS(C)=O.O>[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[NH:31][C:32]([N:13]1[CH2:12][CH2:11][C:10]2([C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:8]([S:5]([CH3:4])(=[O:6])=[O:7])[CH2:9]2)[CH2:15][CH2:14]1)=[O:33]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 13101074Phenyl 1,3-benzothiazol-2-ylcarbamateHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

Product 1

HCID 12108782N-(2-benzothiazolyl)-1-methylsulfonylspiro[indoline-3,4'-piperidine]-1'-carboxamideYield 85.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

10 M aqueous NaOH solution (75 uL) was added to a solution of 1-methylsulfonylspiro[indoline-3,4′-piperidine]hydrochloride 2-1 (225 mg, 0.74 mmol) in DMSO (2.5 mL). Phenyl N-(2-benzothiazolyl)carbamate 2-2 (200 mg, 0.74 mmol) was added to the mixture, and the resulting mixture was stirred at room temperature for 20 h. The mixtrue was diluted with water and extracted with EtOAc. The organic extract was washed with dil. NaOH and brine, and dried over Na2SO4. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 200 (279 mg, 85%) as a colorless amorphous solid.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with dil. NaOH and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1190657c8954190b154829b5b339b62
Source dataset
uspto-grants-2002_12
Patent number
US06495559B2

Reaction notes

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