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

HRID 1279351Notes

Reaction equation

HRID 1279351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:29][CH2:30][OH:31])[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:28])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:39][S:40]([O:31][CH2:30][CH2:29][C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:28])[C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)[CH2:10]1)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 184275132-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol

Product 1

HCID 577562112-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol methanesulfonateYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

388 mg (0.83 mmole) of 2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol [prepared as described in step (e) above] were dissolved in 5 ml of methylene chloride, and 126 mg (1.25 mmole) of triethylamine and 0.078 ml (1.01 mmole) of methanesulfonyl chloride were added to the resulting solution. The mixture was then stirred at room temperature for 2 hours. The reaction mixture was then diluted with methylene chloride, after which it was washed with 1 N aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, in that order. The organic extract was dried over anhydrous sodium sulfate, and then 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 hexane and ethyl acetate ranging from 1:4 to 0:1 by volume as the eluent, to obtain 424 mg of the title compound.

Workup

  1. washafter which it was washed with 1 N aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, in that order
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washa gradient elution method

Sources & evidence

ORD record
ord-bde3766d15a9499b8fab0896919cd517
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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