Aluminium lithium hydride → [3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-dimethylamine

HRID 2120241Notes

Reaction equation

HRID 2120241 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:20])[C:12]=1[CH2:13][CH2:14][C:15]([N:17]([CH3:19])[CH3:18])=O>O1CCCC1.[OH-].[Na+]>[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:20])[C:12]=1[CH2:13][CH2:14][CH2:15][N:17]([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 234390693-(2,4-dimethyl-1H-pyrrol-3-yl)-N,N-dimethyl-propionamide

Product 1

HCID 23439033[3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-dimethylamineYield 75.4%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To the suspension of lithium aluminum hydride (2.3 g, 60 mmol) in tetrahydrofuran (50 mL) was added a solution of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-N,N-dimethyl-propionamide (9.81 g, 50 mmol) in THF (50 mL) dropwise. The reaction mixture was stirred at 80° C. for 1 hour and cooled with ice bath. Ice cube was added into the reaction mixture slowly until no more gas generated. A few drops of 2 N sodium hydroxide was added and the reaction mixture was stirred at room temperature for 30 minutes, extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give 6.8 g (75%) of [3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-dimethylamine as an orange oil which was used without further purification.

Workup

  1. temperaturecooled with ice bath
  2. additionIce cube was added into the reaction mixture slowly until no more gas
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a0c44d9c5e9045fcb033284dee51bc0b
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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