N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine → 4-(1-(Diethylamino)-2-methylpropan-2-yl)aniline

HRID 2423227Notes

Reaction equation

HRID 2423227 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][C:5]([CH3:16])([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:6])[CH3:2]>[Pd].C(OCC)(=O)C>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:6])[CH3:16])[CH3:18]

Participants

4

Reactant 1

HCID 67242349N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine

Product 1

HCID 672414654-(1-(Diethylamino)-2-methylpropan-2-yl)anilineYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round bottomed flask was charged N,N-diethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine (1.45 g, 5.79 mmol), ethyl acetate (29 mL) and a nitrogen atmosphere was introduced to the flask. 10% Palladium on activated carbon was carefully introduced and the flask contents were purged (evacuate—backfill) twice with nitrogen and lastly with hydrogen dispensed from a balloon. The reaction was stirred for 16 h under the hydrogen atmosphere. The hydrogen was removed and the solution was filtered over Celite®, rinsed with methanol and the filtrate was concentrated in vacuo to give 4-(1-(diethylamino)-2-methylpropan-2-yl)aniline (1.19 g, 93.5%) as a light yellow oil. LC/MS (ESI+) 221 (M+H)+.

Workup

  1. additiona nitrogen atmosphere was introduced to the flask
  2. customthe flask contents were purged
  3. custom(evacuate—backfill) twice with nitrogen
  4. customThe hydrogen was removed
  5. filtrationthe solution was filtered over Celite®
  6. washrinsed with methanol
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c02448c117354a8a9f425b8525f5b8ae
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

Loading…