Ethanol → HCID 68717165, compound

HRID 1159829Notes

Reaction equation

HRID 1159829 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH2:22][N:23]([CH3:25])[CH3:24])=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9](S(C1C=CC=CC=1)(=O)=O)[CH:8]=[CH:7]2)[CH3:2].CCO.[OH-].[Na+]>O>[CH2:1]([O:3][C:4]1[C:5]([CH2:22][N:23]([CH3:24])[CH3:25])=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 59513540HCID 59513540, compound

Product 1

HCID 68717165HCID 68717165, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

{[5-Ethoxy-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}dimethylamine (655 mg, 1.831 mmol; Example 133) was added EtOH (5 ml) and 2 M NaOH (5 ml) and heated at 70 oC for 5 h. Water was added and white material precipitated. The mixture was extracted with DCM. The organic phase was extracted with 1 M HCl (3×20 ml). The aqueous phase was made alkaline (pH 9) using 2 M NaOH and extracted with DCM (3×50 ml). The combined organic layers were dried (MgSO4) and evaporated. Yield: 293 mg (74%); brown oil. MS (ESI+) for C13H18N2O m/z 219 (M+H)+.

Workup

  1. temperatureheated at 70 oC for 5 h
  2. customwhite material precipitated
  3. extractionThe mixture was extracted with DCM
  4. extractionThe organic phase was extracted with 1 M HCl (3×20 ml)
  5. extractionextracted with DCM (3×50 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-39467441af11456892e5d83f2223462e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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