Trifluoroacetic acid → (3-Methoxy-4((6-methylpyridin-3-yl)methoxy)phenyl)methanamine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[CH2:6][NH:7]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][NH2:7])[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of tert-butyl 3-methoxy-4-((6-methylpyridin-3-yl)methoxy)benzylcarbamate (29.74 g, 82.97 mmol) in dichloromethane (100 mL) was added trifluoroacetic acid (50 mL, 649.0 mmol). The resulting brown solution was allowed to stir at room temperature. After 2 h, the reaction mixture was concentrated to dryness, and the residue was dissolved in water (250 mL). The acidic solution was extracted with diethyl ether (2×125 mL; organic phases discarded). The aqueous phase was then made basic with concentrated ammonium hydroxide. The basic aqueous phase was then extracted with dichloromethane (3×100 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 19.22 g (90%) of (3-methoxy-4-((6-methylpyridin-3-yl)methoxy)phenyl)methanamine as brown solid.
Workup
- concentrationthe reaction mixture was concentrated to dryness
- dissolutionthe residue was dissolved in water (250 mL)
- extractionThe acidic solution was extracted with diethyl ether (2×125 mL; organic phases discarded)
- extractionThe basic aqueous phase was then extracted with dichloromethane (3×100 mL)
- dry with materialThe combined organic phases were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-427a3e92d8654c35b4e347ff95002468
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067914B1
Reaction notes
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