Pyridine → 1-{4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazin-1-yl}ethanone

HRID 2105988Notes

Reaction equation

HRID 2105988 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([OH:28])([CH2:15][C:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])([CH3:18])[CH3:17])[C:11]([F:14])([F:13])[F:12])[CH2:3]1.N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[F:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[C:19]([C:16]([CH3:18])([CH3:17])[CH2:15][C:10]([OH:28])([C:11]([F:12])([F:13])[F:14])[CH2:9][N:4]2[CH2:3][CH:2]([CH3:1])[N:7]([C:35](=[O:37])[CH3:36])[CH:6]([CH3:8])[CH2:5]2)[CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57809802HCID 57809802, compound

Product 1

HCID 103664031-{4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazin-1-yl}ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,5-dimethylpiperazin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (18 mg) in methylene chloride (1 mL) was added pyridine (55.8 μL) followed by acetic anhydride (43.4 μL). The resulting mixture was stirred overnight, quenched with saturated aqueous sodium bicarbonate solution and extracted twice with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 50% ethyl acetate-hexanes) to give the title compound as a clear oil (20 mg).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography with silica gel (eluted with 50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-cdce3900379f41e99cd1e873895f3daa
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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