Ethyl Acetate → 3-[2-(Dimethylamino)ethoxy]benzenemethanamine
Reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C1COCC1>[NH2:10][CH2:9][C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
3-(2-Dimethylamino-ethoxy)-benzonitrile (0.8 g, 1 eq, 4.1 mmol) was dissolved in THF (80 mL) and cooled down to 0-5° C. A 1.0 M solution of lithium aluminium hydride in THF (0.47 g, 3.0 eq, 12.3 mmol) was added at 0-5° C. The reaction mixture was allowed to warm to RT and was stirred for 4 hrs. After completion of the reaction (confirmed by TLC), ethyl acetate at 0-5° C. was slowly added to quench any excess of lithium aluminium hydride in the reaction mixture, followed by addition of saturated sodium sulphate solution (2 mL). The reaction mass was filtered through hy-flow bed and the filtrate was concentrated in vacuo to obtain the crude product.
Workup
- temperatureto warm to RT
- additionwas slowly added
- customto quench any excess of lithium aluminium hydride in the reaction mixture
- additionfollowed by addition of saturated sodium sulphate solution (2 mL)
- filtrationThe reaction mass was filtered through hy-flow bed
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-01cf25dcdb7343698430e9ed08b382dd
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716473B2
Reaction notes
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