Diethyl[2-(4-nitrophenoxy)ethyl]amine → 4-(2-(Diethylamino)ethoxy)aniline

HRID 2067863Notes

Reaction equation

HRID 2067863 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:16]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:17]

Participants

4

Reactant 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Product 1

HCID 4189324-(2-(Diethylamino)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine 2 (14.0 mmol) in MeOH (20 mL), in a Parr pressure bottle, is added Pd (10% on carbon, 50% wet, 10% weight). The suspension is shaken at 50 psi of H2 for 2 h. The reaction mixture is filtered through celite. The solvent is removed and the residue is dissolved in MeOH (20 mL) and treated with HCl (1 eq of a 4N solution in dioxane) to afford 4-(2-diethylamino-ethoxy)-phenylamine 3 as hydrochloride salt. 1H NMR (400 MHz, d6-DMSO) δ 6.98-6.91 (m, 4H), 4.30 (t, J=4.0 Hz, 2H), 3.47 (t, J=4.0 Hz), 3.20 (m, 4H), 1.24 (t, J=8.0 Hz, 6H). MS (m/z) (M+1)+: 209.3.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. customThe solvent is removed
  3. dissolutionthe residue is dissolved in MeOH (20 mL)
  4. additiontreated with HCl (1 eq of a 4N solution in dioxane)

Sources & evidence

ORD record
ord-3586f67765ab4df59e91275a5c85dfee
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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