Triethylamine → N-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-N-methyl-2-(4-acetylamino-2-isopropyl-5-methylphenoxy)ethylamine

HRID 55387Notes

Reaction equation

HRID 55387 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[CH:8][C:7]=1[CH:17]([CH3:19])[CH3:18].[CH3:20][O:21][C:22]1[C:29]([CH3:30])=[C:28]([CH3:31])[C:27]([O:32][CH3:33])=[C:26]([CH3:34])[C:23]=1[CH2:24]Cl.C(N(CC)CC)C>CN(C)C=O>[CH3:20][O:21][C:22]1[C:29]([CH3:30])=[C:28]([CH3:31])[C:27]([O:32][CH3:33])=[C:26]([CH3:34])[C:23]=1[CH2:24][N:2]([CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14](=[O:16])[CH3:15])=[CH:8][C:7]=1[CH:17]([CH3:19])[CH3:18])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108789291-(Chloromethyl)-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 19957678N-Methyl-2-(4-acetylamino-2-isopropyl-5-methylphenoxy)ethylamine

Product 1

HCID 19957658N-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-N-methyl-2-(4-acetylamino-2-isopropyl-5-methylphenoxy)ethylamineYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Methyl-2-(4-acetylamino-2-isopropyl-5-methylphenoxy)ethylamine (4.94 g) and 2,5-dimethoxy-3,4,6-trimethylbenzyl chloride (4.29 g) were dissolved in N,N-dimethylformamide (70 ml), and triethylamine (1.89 g) was added dropwise while stirring the mixture at room temperature. The mixture was stirred at room temperature for 16.5 hours. After the reaction, the solvent was distilled off, and water was added. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1) to give 6.40 g of a pale-yellow solid. A portion (1.0 g) was taken therefrom and recrystallized from diisopropyl ether to give 0.62 g of the title compound (colorless crystals).

Workup

  1. stirringThe mixture was stirred at room temperature for 16.5 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1)

Sources & evidence

ORD record
ord-f9a8a70d8a224fc19a8a03acae303de4
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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