4-Aminophenol → 4-[2-(Dimethylamino)ethoxy]aniline

HRID 43053Notes

Reaction equation

HRID 43053 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[OH-].[Na+]>CN(C=O)C>[CH3:6][N:5]([CH3:7])[CH2:4][CH2:3][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 64846554-[2-(Dimethylamino)ethoxy]anilineYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-2-dimethylaminoethane hydrochloride (2 g, 21.9 mmol, 1.2 equiv) was added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.8 g, 45.8 mmol, 2.5 equiv) in DMF (27 mL), under an argon atmosphere. The reaction mixture was stirred for 17 h at rt. The resulting dark suspension was filtered. The filtrate was diluted with DCM (200 ml) and washed with brine (2×50 mL). The organic phase was dried (Na2SO4), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH, 7:3) provided 3 g of the title compound as a brown solid: API-MS: 181.2 [M+H]+; TLC: Rf=0.18 (DCM/MeOH, 7:3).

Workup

  1. filtrationThe resulting dark suspension was filtered
  2. additionThe filtrate was diluted with DCM (200 ml)
  3. washwashed with brine (2×50 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (DCM/MeOH, 7:3)

Sources & evidence

ORD record
ord-8f2e52d0390449dc9f2d61d478ed0dd6
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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