Sodium Hydroxide → N,N-Dimethyl 4-(4-aminophenyl)butanamide

HRID 240817Notes

Reaction equation

HRID 240817 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:23])[C:5](=[O:22])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15]C(=O)C(F)(F)F)=[CH:11][CH:10]=1>CO>[CH3:23][N:4]([CH3:3])[C:5](=[O:22])[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59296549N,N-Dimethyl 4-[4-(2,2,2-Trifluoroacetylamino)phenyl]butanamide2×

Product 1

HCID 59296636N,N-Dimethyl 4-(4-aminophenyl)butanamideYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH solution (3 mL) was added to a solution of N,N-Dimethyl 4-[4-(2,2,2-Trifluoroacetylamino)phenyl]butanamide (Formula 46) (0.17 g, 0.55 mmol) in methanol (2 mL) at room temperature. The mixture was stirred for 14 hour. The mixture was partitioned with chloroform (25 mL) and water (25 mL). The organic layer was dried over MgSO4, and concentrated and the residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1) to give N,N-Dimethyl 4-(4-aminophenyl)butanamide (Formula 47) (74 mg, 66%) as a white solid. 1H NMR δ 6.97 (d, 2H, J=8.3 Hz), 6.61 (d, 2H, J=8.3 Hz), 3.56 (br s, 2H), 2.92 (s, 6H), 2.56 (t, 2H, J=7.7 Hz), 2.28 (t, 2H, J=7.7 Hz), 1.91 (p, 2H, J=7.7 Hz).

Workup

  1. customThe mixture was partitioned with chloroform (25 mL) and water (25 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1)

Sources & evidence

ORD record
ord-525c808017d14ccca55adc38c416a5f6
Source dataset
uspto-grants-2014_02
Patent number
US08648105B2

Reaction notes

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