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

HRID 55383Notes

Reaction equation

HRID 55383 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([OH:21])=[CH:16][C:15]=1[CH:22]([CH3:24])[CH3:23].[OH:25][C:26]1[C:27]([CH3:40])=[C:28]([C:31]([O:36][CH2:37][CH2:38][OH:39])=[C:32]([CH3:35])[C:33]=1[CH3:34])[CH2:29][Cl:30]>CN(C)C=O>[ClH:30].[OH:25][C:26]1[C:27]([CH3:40])=[C:28]([C:31]([O:36][CH2:37][CH2:38][OH:39])=[C:32]([CH3:35])[C:33]=1[CH3:34])[CH2:29][N:10]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([OH:21])=[CH:16][C:15]=1[CH:22]([CH3:24])[CH3:23])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199577083-Hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl chlorideHCID 67726891N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochloride

Product 1

HCID 19957689N-{3-hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl}-N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochlorideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (2.8 ml) was added dropwise to a solution of N-methyl-2-(4-hydroxy-2-isopropyl-5-methylphenoxy)ethylamine hydrochloride (2.60 g) and 3-hydroxy-6-(2-hydroxyethoxy)-2,4,5-trimethylbenzyl chloride (2.45 g) in N,N-dimethylformamide (20 ml), and the mixture was stirred at room temperature for 16 hours. After the completion of the reaction, the reaction mixture was poured on ice water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give 3.8 g of a pale brown oil. The oil was dissolved in a small amount of methanol and conc. hydrochloric acid (1.2 ml) was added. The solvent was distilled off under reduced pressure and the residue was recrystallized from ethanol-diethyl ether to give 2.9 g of the title compound (colorless crystals).

Workup

  1. customAfter the completion of the reaction
  2. additionthe reaction mixture was poured on ice water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f8e8fd70ccd4e9f9a30c97dc3d5de11
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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