1-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-3,5-dimethylpiperidine → 4-[2-(3,5-Dimethylpiperidin-1-yl)ethoxy]-3-methoxyphenylamine

HRID 735132Notes

Reaction equation

HRID 735132 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH:12]([CH3:14])[CH2:11][CH:10]([CH3:15])[CH2:9]1>ClCCl.CO>[CH3:14][CH:12]1[CH2:11][CH:10]([CH3:15])[CH2:9][N:8]([CH2:7][CH2:6][O:5][C:4]2[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:3]=2[O:2][CH3:1])[CH2:13]1

Participants

3

Reactant 1

HCID 688195601-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-3,5-dimethylpiperidine

Product 1

HCID 688167904-[2-(3,5-Dimethylpiperidin-1-yl)ethoxy]-3-methoxyphenylamine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 3.1.b. from 1-[2-(2-methoxy-4-nitrophenoxy)ethyl]-3,5-dimethylpiperidine. Yield: 0.35 g (96.9% of theory); C15H24N2O2 (M=264.37); calc.: molecular ion peak (M+H)+: 279; found: molecular ion peak (M+H)+: 279; Rf value: 0.3 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 3.1.b

Sources & evidence

ORD record
ord-3d2bc9ae9b48443aafa4be2f3be2f837
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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