Hydrochloric Acid → [2-(3-Aminophenoxy)ethyl]dimethylamine dihydrochloride

HRID 419310Notes

Reaction equation

HRID 419310 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[ClH:11].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][Cl:16].Cl>CN(C=O)C.O>[ClH:16].[ClH:11].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115683-AminophenolHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 66649609[2-(3-Aminophenoxy)ethyl]dimethylamine dihydrochlorideYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 3-aminophenol (10.9 g, 100 mmol) in DMF (100 mL) cooled with an ice/H2O bath was added NaH (8.90 g, 222 mmol) in 4 portions. 2-(Dimethylamino)ethylchloride hydrochloride (15.8 g, 110 mmol) was then added in 3 portions and the reaction was stirred at rt overnight. The reaction was poured into H2O (600 mL) and extracted with EtOAc. The combined organic layer was washed with brine, dried (MgSO4) and concentrated. Purification by flash column chromatography (flash chromatography), treatment with HCl (50.0 mL, 4M in dioxane, 200 mmol) and concentration provided the title compound (14.0 g, 56.0 mmol, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.80 (s, 6H), 3.46 (t, J=4.8 Hz, 2H), 4.30 (t, J=4.9 Hz, 2H), 6.58-6.66 (m, 3H), 7.18 (t, J=8.2 Hz, 1H), 8.55 (br.s., 2H), 10.70 (br.s., 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (flash chromatography), treatment

Sources & evidence

ORD record
ord-f4aaae4208f44ce097bf09736421bb9d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…