Aluminium lithium hydride → 4-[3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-morpholine
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:23])[C:12]=1[CH2:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=O>O1CCCC1.[OH-].[Na+]>[CH3:7][C:8]1[NH:9][CH:10]=[C:11]([CH3:23])[C:12]=1[CH2:13][CH2:14][CH2:15][N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of lithium aluminum hydride (2.67 g, 70 mmol) in tetrahydrofuran (100 ml) was added dropwise a solution of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-morpholin-4-yl-propan-1-one (13.84 g, 59 mmol) in tetrahydrofuran (50 ml). The reaction mixture was stirred at 80° C. for 1 hour and cooled ins an ice bath. Ice was added to the reaction mixture slowly until gas evolution ceased. A few drops of 2N sodium hydroxide were added and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was then extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to give 10.37 g (79%) of 4-[3-(2,4-dimethyl-1H-pyrrol-3-yl)-propyl]-morpholine as a light brown oil which was used without further purification.
Workup
- temperaturecooled ins an ice bath
- additionIce was added to the reaction mixture slowly until gas evolution
- stirringthe reaction mixture was stirred at room temperature for 30 minutes
- extractionThe reaction mixture was then extracted with ethyl acetate
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3c158734bf6d47d1ae5be013041997da
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119090B2
Reaction notes
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