Triethylamine → 2-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol

HRID 1279350Notes

Reaction equation

HRID 1279350 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][OH:17])[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31].C(=O)([O-])O.[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:30](=[O:31])[C:29]3[CH:28]=[C:27]([O:26][CH3:25])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 154727472-[2-(3,4-Dichlorophenyl)morpholin-2-YL]ethanol

Product 1

HCID 184275132-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanolYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.28 g (4.63 mmole) of 2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol [prepared as described in step (d) above] were dissolved in 30 ml of methylene chloride, and 2.66 g (26.3 mmole) of triethylamine, 1.28 g (5.55 mmole) of 3,4,5-trimethoxybenzoyl chloride and 5 mg of 4-dimethylaminopyridine were added to the resulting solution. The mixture was then stirred at room temperature for 6 hours. At the end of this time, the reaction solution was poured into an aqueous solution of sodium hydrogencarbonate and extracted with methylene chloride. The extract was then washed with a saturated aqueous solution of sodium chloride. The organic extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of methylene chloride and acetone ranging from 4:1 to 7:3 by volume as the eluent, to obtain 1.72 g of the title compound.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was then washed with a saturated aqueous solution of sodium chloride
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washa gradient elution method

Sources & evidence

ORD record
ord-7da4b6fa27d24878b736c43f72ac3cec
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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