Water → (4-(4-methylpiperazine-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)phenyl)methanol
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([N:17]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)C(=O)C(F)(F)F)[CH:9]=2)[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[C:10]([NH:17][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:9]=2)[CH2:6][CH2:7]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
500 mg (1.060 mmol) of 4-(4-methylpiperazine-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzoic acid dissolved in 5 ml of tetrahydrofuran is added at 0° C. to a suspension of 201 mg (5.30 mmol) of LiAlH4 in 9 ml of tetrahydrofuran. The reaction mixture is stirred at 0° C. for 1 hour and then at room temperature for 3 hours. The reaction mixture is cooled at 0° C. and then, drop by drop, 200 μl water, then 200 μl of soda solution (15% by weight) and finally 1 ml of water are added. The reaction mixture is stirred at room temperature for 2 hours and then filtered and rinsed with tetrahydrofuran. The filtrate is concentrated to yield 250 mg (yield=77%) of (4-(4-methylpiperazine-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)phenyl)methanol in the form of a white solid.
Workup
- waitat room temperature for 3 hours
- temperatureThe reaction mixture is cooled at 0° C.
- stirringThe reaction mixture is stirred at room temperature for 2 hours
- filtrationfiltered
- washrinsed with tetrahydrofuran
- concentrationThe filtrate is concentrated
Sources & evidence
- ORD record
- ord-fd15eb666e13435ea3b01abf04143613
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09381195B2
Reaction notes
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