1-[2-(3-Methoxy-4-nitro-phenoxy)-ethyl]-piperidine → 2-Methoxy-4-[2-(piperidin-1-yl)ethoxy]aniline

HRID 448399Notes

Reaction equation

HRID 448399 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:15]=[CH:16][C:17]=1[NH2:18]

Participants

5

Reactant 2

HCID 583072481-[2-(3-Methoxy-4-nitro-phenoxy)-ethyl]-piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 552339672-Methoxy-4-[2-(piperidin-1-yl)ethoxy]anilineYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[2-(3-methoxy-4-nitro-phenoxy)-ethyl]-piperidine (1.5 g, 5.4 mmol) and 5% Pd—C (0.5 g) in ethyl acetate (70 mL) was shaken under 50 psi of hydrogen for 18 hours. The mixture was filtered through Celite and evaporated, providing 1.1 g of the product, in 81% yield: 1H NMR (DMSO-d6) δ 1.45-1.53 (m, 6H), 2.35-2.41 (m, 4H), 2.59 (t, J=6.0 Hz, 2H), 3.74 (s, 3H), 3.93 (t, J=6.0 Hz, 2H), 6.28 (dd, J=8.3 Hz, J=2.6 Hz, 1H), 6.45 (d, J=2.6 Hz, 1H), 6.63 (d, J=8.3 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-eab36d6e23e4420e9b5129121518f9a9
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

Loading…