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

HRID 55388Notes

Reaction equation

HRID 55388 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[C:10]([CH3:21])=[C:11]([C:14]([O:19][CH3:20])=[C:15]([CH3:18])[C:16]=1[CH3:17])[CH2:12]Cl.[CH3:22][NH:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1[CH:34]([CH3:36])[CH3:35]>CN(C)C=O>[OH:8][C:9]1[C:10]([CH3:21])=[C:11]([C:14]([O:19][CH3:20])=[C:15]([CH3:18])[C:16]=1[CH3:17])[CH2:12][N:23]([CH2:24][CH2:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1[CH:34]([CH3:36])[CH3:35])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109218743-Hydroxy-6-methoxy-2,4,5-trimethylbenzyl chlorideHCID 19957700N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamine

Product 1

HCID 19957653N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamineYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (7.0 ml) was added dropwise to a solution of 3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl chloride (10.73 g) and N-methyl-2-(2-isopropyl-5-methylphenoxy)ethylamine (10.37 g) in N,N-dimethylformamide (60 ml) while stirring the mixture at room temperature. Immediately after the dropwise addition, heat was developed and salt was precipitated. The mixture was stirred at room temperature for 2 hours and triethylamine (2.0 ml) was added. The mixture was stirred for 1 hour. The reaction mixture was poured on ice water and extracted with ethyl acetate to give a crude product. The product was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1) to give 18.03 g of the title compound (pale brown solid).

Workup

  1. additionImmediately after the dropwise addition
  2. temperatureheat
  3. customsalt was precipitated
  4. stirringThe mixture was stirred at room temperature for 2 hours
  5. additiontriethylamine (2.0 ml) was added
  6. stirringThe mixture was stirred for 1 hour
  7. additionThe reaction mixture was poured on ice water
  8. extractionextracted with ethyl acetate
  9. customto give a crude product
  10. customThe product was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1)

Sources & evidence

ORD record
ord-5203103535ef4ddfab21bf161f425d1f
Source dataset
uspto-grants-1997_04
Patent number
US05624961

Reaction notes

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