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

HRID 55384Notes

Reaction equation

HRID 55384 reaction equation
[C:1]([NH:4][C:5]1[C:14]([CH3:15])=[CH:13][C:8]([O:9][CH2:10][CH2:11][NH2:12])=[C:7]([CH:16]([CH3:18])[CH3:17])[CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[OH:26][C:27]1[C:28]([CH3:39])=[C:29]([C:32]([O:37][CH3:38])=[C:33]([CH3:36])[C:34]=1[CH3:35])[CH2:30]Cl>CN(C)C=O>[OH:26][C:27]1[C:28]([CH3:39])=[C:29]([C:32]([O:37][CH3:38])=[C:33]([CH3:36])[C:34]=1[CH3:35])[CH2:30][NH:12][CH2:11][CH2:10][O:9][C:8]1[CH:13]=[C:14]([CH3:15])[C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109218743-Hydroxy-6-methoxy-2,4,5-trimethylbenzyl chlorideHCID 199577142-(4-Acetylamino-2-isopropyl-5-methylphenoxy)ethylamine

Product 1

HCID 19957661N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-2-(4-acetylamino-2-isopropyl-5-methylphenoxy)ethylamineYield 5.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(4-Acetylamino-2-isopropyl-5-methylphenoxy)ethylamine (1.0 g) and triethylamine (0.50 g) were dissolved in N,N-dimethylformamide (20 ml), and 3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl chloride (0.86 g) dissolved in N,N-dimethylformamide (10 ml) was added dropwise while stirring the mixture at room temperature. The mixture was stirred for 5 hours. After the completion of the reaction, the solvent was distilled off, and water and ethyl acetate were added. The mixture was stirred and an insoluble matter was collected by filtration. The obtained solid was recrystallized from ethyl acetate to give 100 mg of the title compound.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 5 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off
  5. additionwater and ethyl acetate were added
  6. stirringThe mixture was stirred
  7. filtrationan insoluble matter was collected by filtration
  8. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a4b0db77e7704429b9a2a0480f4d84fc
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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