Potassium Hydroxide → HCID 20698842, compound

HRID 382467Notes

Reaction equation

HRID 382467 reaction equation
C([O:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:24][C@H:25]([NH:27][CH2:28][CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH2:38][CH3:39])[CH3:26])=[CH:19][C:20]=2[C:22]#[N:23])[CH2:15][CH2:14]1)(=O)C1C=CC=CC=1.[OH-].[K+]>CO.O>[CH2:38]([O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[O:30][CH2:29][CH2:28][NH:27][C@H:25]([CH3:26])[CH2:24][C:18]1[CH:17]=[C:16]2[C:21](=[C:20]([C:22]#[N:23])[CH:19]=1)[N:13]([CH2:12][CH2:11][CH2:10][OH:9])[CH2:14][CH2:15]2)[CH3:39]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69833306HCID 69833306, compound

Product 1

HCID 20698842HCID 20698842, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(R)-3-[7-Cyano-5-[2-[[2-(2-ethoxyphenoxy)ethyl]-amino]propyl]-2,3-dihydro-1H-indol-1-yl]propyl benzoate (7.23 g) was dissolved in methanol (46 ml) and the solution was added to a solution of potassium hydroxide (1.54 g) in distilled water (9.2 ml). After being heated under reflux for 1 hour, the reaction mixture was concentrated in vacuo. Distilled water (100 ml) was added to the residue and the resulting mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was dissolved in toluene(30 ml) and the toluene was removed in vacuo to give (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-1-(3-hydroxypropyl)-2,3-dihydro-1H-indole-7-carbonitrile(6.06 g) as a pale brown oil.

Workup

  1. temperatureAfter being heated
  2. temperatureunder reflux for 1 hour
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionDistilled water (100 ml) was added to the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. dissolutionthe residue was dissolved in toluene(30 ml)
  10. customthe toluene was removed in vacuo

Sources & evidence

ORD record
ord-1fc9a3a51f054417b9d98e7c820c146c
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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