Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([OH:16])=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2([CH2:33][CH2:34][OH:35])[O:32][CH2:31][CH2:30][NH:29][CH2:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26]>C(#N)C>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([N:29]2[CH2:30][CH2:31][O:32][C:27]([CH2:33][CH2:34][OH:35])([C:22]3[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=3)[CH2:28]2)=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,5-bis(trifluoromethyl)phenylacetic acid (2.0 g, 7.4 mmol) in acetonitrile (20 ml), N,N′-carbonyldiimidazole (1.3 g, 8.1 mmol) was added at room temperature, then 2-[2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol (2.4 g, 8.8 mmol) was further added, and the resulting mixture was stirred at room temperature for one hour. After completion of the reaction, the reaction mixture was evaporated to dryness. To the obtained residue, methylene chloride (20 ml), water (20 ml) and concentrated hydrochloric acid (2 ml) were added, and the resulting mixture was partitioned. The separated organic layer was washed successively with a 5% aqueous solution of sodium hydroxide (25 ml) and water (20 ml) and evaporated to dryness to afford the title compound [2.3 g, yield: 58.6%] as an oil.
Workup
- customAfter completion of the reaction
- customthe reaction mixture was evaporated to dryness
- additionTo the obtained residue, methylene chloride (20 ml), water (20 ml) and concentrated hydrochloric acid (2 ml) were added
- customthe resulting mixture was partitioned
- washThe separated organic layer was washed successively with a 5% aqueous solution of sodium hydroxide (25 ml) and water (20 ml)
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-55f01e0ef7054611848a4ecce95d2639
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560549B2
Linked notes
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