2-(2-Isopropyl-5-methylphenoxy)ethanamine → N-(3-ethoxy-6-hydroxy-2,4,5-trimethylbenzyl)-2-(2-isopropyl-5-methylphenoxy)ethylamine

HRID 55390Notes

Reaction equation

HRID 55390 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:15])=[C:6]([C:9]([OH:14])=[C:10]([CH3:13])[C:11]=1[CH3:12])[CH:7]=O)[CH3:2].[CH:16]([C:19]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:20]=1[O:21][CH2:22][CH2:23][NH2:24])([CH3:18])[CH3:17]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[C:5]([CH3:15])=[C:6]([C:9]([OH:14])=[C:10]([CH3:13])[C:11]=1[CH3:12])[CH2:7][NH:24][CH2:23][CH2:22][O:21][C:20]1[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:19]=1[CH:16]([CH3:18])[CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 4250702-(2-Isopropyl-5-methylphenoxy)ethanamineHCID 199576553-Ethoxy-6-hydroxy-2,4,5-trimethylbenzaldehyde

Product 1

HCID 19957686N-(3-ethoxy-6-hydroxy-2,4,5-trimethylbenzyl)-2-(2-isopropyl-5-methylphenoxy)ethylamineYield 79.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-ethoxy-6-hydroxy-2,4,5-trimethylbenzaldehyde (2.08 g) and 2-(2-isopropyl-5-methylphenoxy)ethylamine (1.93 g) in benzene (50 ml) was refluxed under heating for 6 hours in a Dean-Stark extractor. The solvent was distilled off under reduced pressure and the residue was suspended in ethanol (100 ml). Sodium borohydride (0.40 g) was added with ice-cooling and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure and water was added. The mixture was extracted with ethyl acetate and the obtained extract was purified by silica gel column chromatography (eluent; ethyl acetate/benzene=1/1) to give 3.06 g of a colorless solid. The solid was recrystallized from a mixed solvent of ethanol-methanol to give 1.99 g of the title compound (colorless needle crystals).

Workup

  1. temperatureunder heating for 6 hours in a Dean-Stark extractor
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionSodium borohydride (0.40 g) was added with ice-
  4. temperaturecooling
  5. distillationThe solvent was distilled off under reduced pressure and water
  6. additionwas added
  7. extractionThe mixture was extracted with ethyl acetate
  8. extractionthe obtained extract
  9. customwas purified by silica gel column chromatography (eluent; ethyl acetate/benzene=1/1)

Sources & evidence

ORD record
ord-0eaf87dcf15948718474509a3c2422f7
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

Loading…