Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine → N-[2-(4-Amino-2-methylphenoxy)ethyl]-N,N-diethylamine

HRID 735111Notes

Reaction equation

HRID 735111 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH3:16])[CH3:2]>C(OCC)(=O)C.[Ni]>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:16])[CH3:18]

Participants

4

Reactant 1

HCID 68816853Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine

Product 1

HCID 26189998N-[2-(4-Amino-2-methylphenoxy)ethyl]-N,N-diethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.10 g (12.3 mmol) of diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine is dissolved in 250 mL of ethyl acetate, 0.55 g of Raney nickel is added, and the mixture is hydrogenated for 36 hours at 50 psi and ambient temperature. The catalyst is filtered off and the filtrate is evaporated down in vacuo. Yield: 2.70 g (99% of theory); C13H22N2O (M=222.33); calc.: molecular ion peak (M+H)+: 223; found: molecular ion peak (M+H)+: 223; Rf value: 0.35 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down in vacuo

Sources & evidence

ORD record
ord-95142fe444c1446a85281a31fa89e426
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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