3,5-Bis(trifluoromethyl)phenylacetic acid → 2-[4-{[3,5-Bis(trifluoromethyl)phenyl]acetyl}-2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol

HRID 227553Notes

Reaction equation

HRID 227553 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]=1

Participants

4

Reactant 2

HCID 1235873,5-Bis(trifluoromethyl)phenylacetic acidHCID 154727472-[2-(3,4-Dichlorophenyl)morpholin-2-YL]ethanol

Product 1

HCID 186772052-[4-{[3,5-Bis(trifluoromethyl)phenyl]acetyl}-2-(3,4-dichlorophenyl)morpholin-2-yl]ethanolYield 58.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. customAfter completion of the reaction
  2. customthe reaction mixture was evaporated to dryness
  3. additionTo the obtained residue, methylene chloride (20 ml), water (20 ml) and concentrated hydrochloric acid (2 ml) were added
  4. customthe resulting mixture was partitioned
  5. washThe separated organic layer was washed successively with a 5% aqueous solution of sodium hydroxide (25 ml) and water (20 ml)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-55f01e0ef7054611848a4ecce95d2639
Source dataset
uspto-grants-2009_07
Patent number
US07560549B2

Reaction notes

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