3-Cyclopentylpyridine → 3-Cyclopentylpiperidine
Reaction equation
[CH:1]1([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.Cl.[Pt]=O>[CH:1]1([CH:6]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
5
Reagents, catalysts & solvents 3
Procedure
Platinum oxide (0.2 g, 0.82 mmol) was added as a slurry in ethanol to a solution of 3-cyclopentylpyridine (1 g, 6.8 mmol) in ethanol (15 ml) and concentrated hydrochloric acid (1 ml). The mixture was hydrogenated in a Parr apparatus at 50 psi for 18 hours then filtered through Celite. The filtrate was concentrated in vacuo and the residue partitioned between 10% aqueous sodium carbonate solution and ethyl acetate. The organic layer was dried (MgSO4) and concentrated in vacuo to give the title compound (0.87 g, 84%).
Workup
- filtrationthen filtered through Celite
- concentrationThe filtrate was concentrated in vacuo
- customthe residue partitioned between 10% aqueous sodium carbonate solution and ethyl acetate
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4eda89faef2d4775ae310527e3b24da6
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101892B2
Reaction notes
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