Water → (+/-)2-[(2-Methoxyphenoxy)methyl]-4-(4-trifluoromethylbenzyl)morpholine oxalic acid salt

HRID 1532992Notes

Reaction equation

HRID 1532992 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][NH:9][CH2:8]1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[C:29](=[O:32])([O-:31])[O-].[K+].[K+].[OH2:35]>C(O)C.CCOCC>[C:7]([OH:12])(=[O:35])[C:29]([OH:31])=[O:32].[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:26][CH:25]=2)[CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 11333552Morpholine, 2-[(2-methoxyphenoxy)methyl]-

Product 1

HCID 69688018(+/-)2-[(2-Methoxyphenoxy)methyl]-4-(4-trifluoromethylbenzyl)morpholine oxalic acid salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The crude 2-[(2-methoxyphenoxy)methyl]morpholine (2.0 g, 9.0 mmol) was mixed with 4-trifluoromethylbenzylbromide (2.58 g, 10.8 mmol), potassium carbonate (6.84 g, 49.5 mmol) in ethanol (50 ml) and refluxed for 3.5 h. Water was added and the product was extracted with 2 portions of ethyl acetate. Drying and evaporation gave the crude free base. Dissolution in ether and precipitation with oxalic acid gave a salt that was purified by recrystallization from ethanol and then THF. Yield 430 mg, 10%, mp 101-108° C.

Workup

  1. temperaturerefluxed for 3.5 h
  2. extractionthe product was extracted with 2 portions of ethyl acetate
  3. customDrying
  4. customevaporation
  5. customgave the crude free base
  6. customprecipitation with oxalic acid
  7. customgave a salt that
  8. customwas purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-041d9a2b03e34e16a7265a5c40fd8aaa
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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