Tetrahydrofuran → HCID 19600413, compound

HRID 609760Notes

Reaction equation

HRID 609760 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]([CH3:33])[CH3:32])[CH:18]=[CH:17]2)#[N:13].[OH-].[K+]>C(OCC)(=O)C.O>[NH2:13][CH2:12][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]([CH3:33])[CH3:32])[CH:18]=[CH:17]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 19600411HCID 19600411, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19600413HCID 19600413, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 2.3 g of lithium aluminum hydride was added 100 ml of tetrahydrofuran, under stirring condition, and 6 g of 5-cyano-1-[3-(2-isopropyl-imidazol-1-yl)propyl]indole was gradually added thereto. The mixture was refluxed for 4 hours, then after confirmation of that the reaction was finished, under cooling at 0° C., 2.3 ml of water, 2.3 ml of 10% aqueous solution of potassium hydroxide and 7 ml of water were gradually added thereto. The reaction mixture was diluted with ethyl acetate, then filtrated with Celite, and the solvent was removed by distillation, 5.3 g of 5-aminomethyl-1-[3-(2-isopropylimidazol-1-yl)propyl]indole was obtained in the form of yellow oily product.

Workup

  1. additionwas gradually added
  2. temperatureThe mixture was refluxed for 4 hours
  3. filtrationfiltrated with Celite
  4. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-39f67e0907e3485ea2a82348b2c3c248
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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