4-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-[4-Amino-3-(4-methyl-piperidin-1-yl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 646898Notes

Reaction equation

HRID 646898 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 586385144-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586384884-[4-Amino-3-(4-methyl-piperidin-1-yl)-phenyl]-piperidine-1-carboxylic acid tert-butyl esterYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.090 g, 0.22 mmol) (as prepared in Example 33, step (d)) in methanol (2 mL) was hydrogenated over 10% Pd/C at 12 psi for 2 h. The solution was filtered and concentrated to give 0.085 g (100%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C22H35N3O2, 374.3 (M+H), found 374.1.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-73812d7086354a189dd5ec49eab17ec6
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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