Triethylamine → N-{3-hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl}-N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamine

HRID 55389Notes

Reaction equation

HRID 55389 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[C:10]([CH3:23])=[C:11]([C:14]([O:19][CH2:20][CH2:21][OH:22])=[C:15]([CH3:18])[C:16]=1[CH3:17])[CH2:12]Cl.[CH3:24][NH:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1[CH:36]([CH3:38])[CH3:37]>CN(C)C=O>[OH:8][C:9]1[C:10]([CH3:23])=[C:11]([C:14]([O:19][CH2:20][CH2:21][OH:22])=[C:15]([CH3:18])[C:16]=1[CH3:17])[CH2:12][N:25]([CH2:26][CH2:27][O:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1[CH:36]([CH3:38])[CH3:37])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19957700N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamineHCID 199577083-Hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl chloride

Product 1

HCID 19957701N-{3-hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl}-N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamineYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (2.1 ml) was added dropwise to a solution of 3-hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl chloride (2.45 g) and N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamine (2.07 g) in N,N-dimethylformamide (30 ml), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was poured on ice water and extracted with ethyl acetate. The obtained extract was purified by silica gel column chromatography (eluent; ethyl acetate/benzene=1/1) and recrystallized from methanol-water to give 2.51 g of the title compound (colorless needle crystals).

Workup

  1. additionThe reaction mixture was poured on ice water
  2. extractionextracted with ethyl acetate
  3. extractionThe obtained extract
  4. customwas purified by silica gel column chromatography (eluent; ethyl acetate/benzene=1/1)
  5. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-82b9c8b2bc9d4630a05705aa8234b737
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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