1-[5-(1,1-Dioxo-1,2,3,6-tetrahydro-1lambda6-thiopyran-4-yl)-2-nitro-phenyl]-4-methyl-piperidine → 4-(1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenylamine
Reaction equation
[O:1]=[S:2]1(=[O:24])[CH2:7][CH:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:21]([O-])=O)=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]3)[CH:13]=2)[CH2:4][CH2:3]1>CO.[Pd]>[O:24]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:21])=[C:12]([N:14]3[CH2:15][CH2:16][CH:17]([CH3:20])[CH2:18][CH2:19]3)[CH:13]=2)[CH2:4][CH2:3]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1-[5-(1,1-dioxo-1,2,3,6-tetrahydro-1λ6-thiopyran-4-yl)-2-nitro-phenyl]-4-methyl-piperidine (as prepared in the previous step, 65 mg, 0.19 mmol) and 10% Pd/C (40 mg) in 3 mL of MeOH was stirred at RT under H2 (balloon pressure) for 1 h. The Pd catalyst was removed by filtration on Celite and the filtrate was concentrated to give a white solid. Flash chromatography of the compound on silica gel (5% EtOAc/DCM) gave 42 mg (70%) of the title compound as a white solid: 1H-NMR (CDCl3; 400 MHz): δ 6.82 (s, 1H), 6.76 (d, 1H, J=8.2 Hz), 6.68 (d, 1H, J=8.2 Hz), 3.91 (s, 2H), 3.05-3.16 (m, 6H), 2.67 (dddd, 2H, J=12.0, 12.0, 3.2, 3.2 Hz), 2.57 (dd, 2H, J=11.6, 11.6 Hz), 2.36 (m, 2H), 2.14-2.23 (m, 2H), 1.71-1.79 (m, 2H), 1.51 (m, 1H), 1.24-1.40 (m, 2H), 0.99 (d, 3H, J=6.6 Hz). Mass spectrum (ESI, m/z): Calcd. for C17H26N2O2S, 323.2 (M+H), found 323.2.
Workup
- customThe Pd catalyst was removed by filtration on Celite
- concentrationthe filtrate was concentrated
- customto give a white solid
Sources & evidence
- ORD record
- ord-9601918a5ff14289a604872fb038b95e
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705042B2
Reaction notes
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