Morpholine → 1-Ethyl-4-(4-nitrophenyl)piperidine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][CH2:17]N(C(C)C)C(C)C.C(OS(C(F)(F)F)(=O)=O)C.N1CCOCC1>>[CH2:16]([N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14]1)[CH3:17]Participants
5
Procedure
4-(4-Nitrophenyl)piperidine (255, 500 mg g, 2.4 mmol) was dissolved in 30 mLMeCN. To it were added DIEA (830 μL, 4.8 mmol) and then EtOTf (460 μL, 3.6 mmol). The mixture was stirred at RT for 10 min, and to it was added 0.5 mL morpholine. It was concentrated in vacuo and subjected to silica flash column using 0 to 7% MeOh in DCM to isolate 1-ethyl-4-(4-nitrophenyl)piperidine (259). It was dissolved in 40 mL EtOAc. To it was added 10% Pd/C (0.3 g), and the mixture was hydrogenated using a H2 balloon at RT for overnight. The mixture was filtered through celite, and concentrated in vacuo to give 4-(1-ethylpiperidin-4-yl)aniline (260) (410 mg, 83% overall) as a white solid.
Workup
- concentrationIt was concentrated in vacuo
Sources & evidence
- ORD record
- ord-b9c1b697f7f04f43bd6f44650441b159
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382246B2
Reaction notes
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