Hydrogen Peroxide → HCID 69875931, compound

HRID 382468Notes

Reaction equation

HRID 382468 reaction equation
[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH2:8][NH:9][C@H:10]([CH3:27])[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([C:21]#[N:22])[CH:20]=1)[N:17]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:16][CH2:15]2)[CH3:2].[OH-].[Na+].OO.S([O-])([O-])=[O:37].[Na+].[Na+]>CS(C)=O.O>[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][CH:29]=[CH:28][C:5]=1[O:6][CH2:7][CH2:8][NH:9][C@H:10]([CH3:27])[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([C:21]([NH2:22])=[O:37])[CH:20]=1)[N:17]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:16][CH2:15]2)[CH3:2]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 20698842HCID 20698842, compound

Product 1

HCID 69875931HCID 69875931, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

(R)-5-[2-[[2-(2-Ethoxyphenoxy)ethyl]amino]propyl]-1-(3-hydroxypropyl)-2,3-dihydro-1H-indole-7-carbonitrile (5.95 g) was dissolved in dimethylsulfoxide (16.4 ml), and 5N sodium hydroxide solution (0.25 ml) was added to the solution. To the mixture was added 30% hydrogen peroxide (1.55 ml) keeping inner temperature below 25° C., and the mixture was stirred overnight at an inner temperature of 25-30° C. A solution of sodium sulfite (2.39 g) in distilled water (82 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution, distilled water and brine subsequently, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, the residue was recrystallized from ethyl acetate to give (R)-5-[2-[[2-(2-ethoxyphenoxy)-ethyl]amino]propyl]-1-(3-hydroxypropyl)-2,3-dihydro-1H-indole-7-carboxamide (4.72 g).

Workup

  1. customtemperature below 25° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution
  4. distillationdistilled water and brine subsequently
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-355bfa4db4fa4a7cbcc85390a789f826
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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