Sodium Hydroxide → 4-(Benzofuran-6-yl)piperidine
Reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>ClCCl.FC(F)(F)C(O)=O.O>[O:1]1[C:5]2[CH:6]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1Participants
6
Conditions
- Temperature
- 15 °C
Procedure
Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(1-benzofuran-6-yl)piperidine-1-carboxylate (compound 63.4, 200 mg, 0.66 mmol) in dichloromethane (3 mL) and trifluoroacetic acid (1 mL). The resulting solution was stirred at 15° C. for 1 hour, then the pH was carefully adjusted to =9 with aqueous sodium hydroxide (2 M). The mixture was diluted with H2O (20 mL) and the layers were separated. The aqueous phase was extracted with dichloromethane (4×20 mL) and the combined organic layers were washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a brown oil (150 mg, crude).
Workup
- customInto a 50-mL round-bottom flask, was placed
- customthe layers were separated
- extractionThe aqueous phase was extracted with dichloromethane (4×20 mL)
- washthe combined organic layers were washed with brine (30 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-de275378516f45a19f6098cc91abae52
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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