Trifluoroacetic acid → HCID 68309777, compound

HRID 1021240Notes

Reaction equation

HRID 1021240 reaction equation
COC1C=CC(C[O:8][CH2:9][C:10]2[CH:11]=[C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)[CH:13]=[CH:14][CH:15]=2)=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[N:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:12]3[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=3)[CH2:17][CH2:18]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68310421HCID 68310421, compound

Product 1

HCID 68309777HCID 68309777, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-{[(4-Methoxybenzyl)oxy]methyl}phenyl)-4-(pyridin-4-yl)piperazine (308 mg) was mixed with dichloromethane (2 ml), and TFA (1 ml) was added thereto. The reaction mixture was stirred at room temperature for 1 hour, and then the reaction mixture was concentrated under reduced pressure. To the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and CHCl3, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography to obtain {3-[4-(pyridin-4-yl)piperazin-1-yl]phenyl}methanol (167 mg).

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and CHCl3
  4. dry with materialthe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-28632b2dcab74924adc907f6053ae715
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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