Piperidine → 2-Nitro-5-(piperidin-1-yl)pyridine
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(OCC)(=O)C>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]Participants
7
Conditions
- Temperature
- 80 °C
Procedure
5-Bromo-2-nitropyridine (3.0 g), tetrabutylammonium iodide (0.273 g), potassium carbonate (2.24 g) and piperidine (1.6 mL) were dissolved in DMSO (25 mL) and heated at 80° C. for 12 hours. The mixture was diluted with ethyl acetate, filtered and the filtrate was concentrated in vacuo. To the residue was added water (75 mL) and the precipitate was isolated by filtration. The solid was evaporated three times from toluene to remove residual water and the product was further dried in vacuo to give 6′-nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (2.87 g) as a yellow powder. MS (EI): 207.2 (M+).
Workup
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- additionTo the residue was added water (75 mL)
- customthe precipitate was isolated by filtration
- customThe solid was evaporated three times from toluene
- customto remove residual water
- customthe product was further dried in vacuo
Sources & evidence
- ORD record
- ord-4c801f39c25f4da1a8a314489c0493e0
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482341B2
Reaction notes
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