Sodium borohydride → HCID 18940835, compound

HRID 355991Notes

Reaction equation

HRID 355991 reaction equation
[BH4-].[Na+].[I-].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]1[CH:17]=[N+:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]1[CH2:17][N:18]([CH3:22])[CH2:19][CH2:20][CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18940820HCID 18940820, compound

Product 1

HCID 18940835HCID 18940835, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride in pellets (5.71 g; 0.0396 mol) was added to a cold (~0° C.) stirring mixture of compound of Description 7 [3-[(5-methoxy-1H-indol-3-yl)methyl]-1-methyl-pyridinium iodide] (7.45 g; 0.0196 mol) in methanol (150 ml). The reaction mixture was stirred at 0° C. for 2 hours. The reaction was then quenched with a saturated solution of aqueous sodium carbonate and the solvent (methanol) was evaporated under vacuum. The product was extracted with methylene chloride from the residual alkaline aqueous solution. The organic extract was dried (MgSO4) and evaporated under vacuum. Purification by Flash Chromatography of the crude product using silica gel and elution with methylene chloride/methanol/ammonia (90/10/1) yielded the desired compound. A solution of the desired compound in diethyl ether was saturated with gaseous hydrogen chloride. A white solid was precipitated. The title compound hydrochloride was collected by filtration, washed with diethyl ether and dried under vacuum (3.5 g).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 hours
  2. customThe reaction was then quenched with a saturated solution of aqueous sodium carbonate
  3. customthe solvent (methanol) was evaporated under vacuum
  4. extractionThe product was extracted with methylene chloride from the residual alkaline aqueous solution
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated under vacuum
  8. customPurification by Flash Chromatography of the crude product
  9. washsilica gel and elution with methylene chloride/methanol/ammonia (90/10/1)

Sources & evidence

ORD record
ord-a9763385c8974b84b2fc13e45a907426
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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