Sodium Sulfate → HCID 19936680, compound

HRID 36895Notes

Reaction equation

HRID 36895 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([S:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH2:21])=O)[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([S:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][NH2:21])[CH:17]=3)[N:12]([CH3:22])[CH:11]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 19936669HCID 19936669, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19936680HCID 19936680, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole-5-carboxamide (3.2 g, prepared in Example 73) in dry THF (40 ml) is added dropwise at 0° C. to a suspension of lithium aluminum hydride (LiAlH4, 1.2 g) in anhydrous THF (200 ml). After 10 hours at room temperature, the reaction mixture is hydrolyzed at 0° C. by the addition of a saturated solution of sodium sulfate. After filtration on Celite, the solution is concentrated, taken up with ether and extracted with a dilute solution of hydrochloric acid. The aqueous phase is rendered basic with sodium hydroxide and extracted with methylene chloride. The organic phase is dried over sodium sulfate and concentrated. After chromatography on silica gel (eluent: AcOEt), 3-[(1-methoxypiperidin-4-yl)thio]-1-methyl-1H-indole-5-methanamine (1.8 g) is obtained in the form of a yellowish solid.

Workup

  1. filtrationAfter filtration on Celite
  2. concentrationthe solution is concentrated
  3. extractionextracted with a dilute solution of hydrochloric acid
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ffe52cc2c63436a96f9e7c513cd8fa7
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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