Triethylamine → N-(2-ethoxy-5-hydroxy-3,4,6-trimethylbenzyl)-N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochloride

HRID 55385Notes

Reaction equation

HRID 55385 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([OH:14])=[CH:9][C:8]=1[CH:15]([CH3:17])[CH3:16].[CH2:18]([O:20][C:21]1[C:28]([CH3:29])=[C:27]([CH3:30])[C:26]([OH:31])=[C:25]([CH3:32])[C:22]=1[CH2:23][Cl:24])[CH3:19].C(N(CC)CC)C>CN(C)C=O>[ClH:24].[CH2:18]([O:20][C:21]1[C:28]([CH3:29])=[C:27]([CH3:30])[C:26]([OH:31])=[C:25]([CH3:32])[C:22]=1[CH2:23][N:3]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([OH:14])=[CH:9][C:8]=1[CH:15]([CH3:17])[CH3:16])[CH3:2])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199577112-Ethoxy-5-hydroxy-3,4,6-trimethylbenzyl chlorideHCID 67726891N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochloride

Product 1

HCID 19957679N-(2-ethoxy-5-hydroxy-3,4,6-trimethylbenzyl)-N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochlorideYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochloride (10.4 g), 2-ethoxy-5-hydroxy-3,4,6-trimethylbenzyl chloride (9.15 g) and triethylamine (8.10 g) were dissolved in N,N-dimethylformamide (80 ml), and the mixture was stirred at room temperature for 4 hours. After the reaction, the solvent was distilled off and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting liquid (1.0 g) was dissolved in methanol and conc. hydrochloric acid (0.2 ml) was added. The mixture was concentrated to dryness under reduced pressure. Recrystallization from ethanol-diethyl ether gave 910 mg of the title compound.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionThe resulting liquid (1.0 g) was dissolved in methanol
  9. additionconc. hydrochloric acid (0.2 ml) was added
  10. concentrationThe mixture was concentrated to dryness under reduced pressure
  11. customRecrystallization from ethanol-diethyl ether

Sources & evidence

ORD record
ord-90fae843b7e34b32be9273363dff04aa
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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