HCID 131726477, compound → 2-[2-(Dimethylamino)ethoxy]phenol

HRID 1765080Notes

Reaction equation

HRID 1765080 reaction equation
Cl.C([O:9][C:10]1[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=1[O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])C1C=CC=CC=1>CO.[Pd]>[CH3:16][N:15]([CH3:17])[CH2:14][CH2:13][O:12][C:11]1[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=1[OH:9]

Participants

4

Reactant 1

HCID 131726477HCID 131726477, compound

Product 1

HCID 186162252-[2-(Dimethylamino)ethoxy]phenolYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-{2-[2-(benzyloxy)phenoxy]ethyl}-N,N-dimethylamine (from Step 1; 7.60 g, 28.0 mmol) in MeOH (80 mL) was added 10% Pd/C (0.8 g) and the mixture was hydrogenated at 70 psi and room temperature for 2 h. The reaction mixture was filtered through a pad of Celite® and silica. The solvent was then removed under reduced pressure to give 5.43 g (quantitative yield) of the title compound as off-white crystals: mp 220° C. HRMS m/z calcd for C10H15NO2 (M)+ 181.1103. Found 181.1105. *The corresponding hydrochloride salt has been reported in Bull. Soc. Chim. Fr. 1935, 1737–1741.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite® and silica
  2. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-cb16457bece14826b6a3ad7c5c0dfc19
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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