Hydrochloric Acid → 1-(2,6-Difluoro-4-nitrophenyl)piperidin-4-one
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:21][CH2:20][C:15]2(OCC[O:16]2)[CH2:14][CH2:13]1.O.Cl>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
The crude 8-(2,6-difluoro-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane from the preceding procedure was dissolved in 4:1 acetone:water (100 mL). Concentrated HCl (5 mL) was added, and the resulting mixture was stirred at 50° C. for 8 hours and then cooled to room temperature. The mixture was concentrated in vacuo to approximately 20 mL, which was carefully added to concentrated aq. NaHCO3 (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated with Et2O and hexanes to give a bright-yellow solid that was collected and dried to provide the title compound (7.13 g, 81%).
Workup
- temperaturecooled to room temperature
- concentrationThe mixture was concentrated in vacuo to approximately 20 mL, which
- additionwas carefully added to concentrated aq. NaHCO3 (100 mL)
- extractionextracted with EtOAc (2×100 mL)
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was triturated with Et2O and hexanes
- customto give a bright-yellow solid
- customthat was collected
- customdried
Sources & evidence
- ORD record
- ord-988c24fef22a420dac0c523074b449bb
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937150B2
Reaction notes
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