N-Ethyl-1,2,3,6-tetrahydro-4-(3-(1-methylethoxy)phenyl)pyridine → N-Ethyl-4-(3-(1-methylethoxy)phenyl)piperidine

HRID 397738Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:17])[CH3:18])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

N-Ethyl-1,2,3,6-tetrahydro-4-(3-(1-methylethoxy)phenyl)pyridine (Preparation 44, 2.0 g, 8.16 mmol) was dissolved in ethanol (20 ml) and 5% palladium on carbon (0.2 g) was added. The suspension was heated at 60° C. under hydrogen (20 psi) for 5 h. The mixture was cooled and the solid was removed by filtration through Arbocel™, washing the resultant cake with ethyl acetate. The filtrate was concentrated in vacuo to give the title compound as an oil (2.0 g, 99%) which was used without further purification.

Workup

temperatureThe mixture was cooled
customthe solid was removed by filtration through Arbocel™
washwashing the resultant cake with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-a7bd88c9793b452192f3e6a0804da337
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610711B2

Reaction notes

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