6-amino-3-(N-propionyl-N-n-propylamino)chroman → 6-Amino-3-(di-n-propylamino)chroman
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([N:12]([C:16](=O)[CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) (300 mg, 1.03 mmol) in anhydrous diethyl ether was added LiAlH4 (300 mg, 7.89 mmol). The mixture was stirred for 1.5 hours at room temperature. Excess hydride was quenched by addition water (0.5 ml), 15% sodium hydroxide (0.3 ml) and water (0.9 ml). The mixture was filtered and the solvent evaporated yielding 216 mg (85%) of 23 as an oil.