Trifluoroacetic acid → HCID 178489565, compound

HRID 54203Notes

Reaction equation

HRID 54203 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]2[CH2:20][CH2:19][C:18](O)([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([C@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])[CH2:19][CH2:20]2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 199585471-(2-Methoxyphenyl)-4-[1-hydroxy-1-(2,4-dimethylphenyl)cyclohex-4-yl]piperazine

Product 1

HCID 178489565HCID 178489565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-methoxyphenyl)-4-[1-hydroxy-1-(2,4-dimethylphenyl)cyclohex-4-yl]piperazine in dichloromethane (anhydrous) at room temperature was added trifluoroacetic acid (8 equivalents). The solution was stirred overnight. Excess trifluoroacetic acid was removed under vacuo and the residue poured into sodium bicarbonate solution. The neutralised aqueous layer was extracted with dichloromethane, washed with salt solution, dried (MgSO4) and filtered. The solvent was removed and the residue purified by silica gel pressure column chromatography using hexane/ether (2/1) as eluant. The solid residue was recrystallised from ether to give the title compound which was converted to its dihydrochloride, m.p. 219° C. (dec.).

Workup

  1. customExcess trifluoroacetic acid was removed under vacuo
  2. additionthe residue poured into sodium bicarbonate solution
  3. extractionThe neutralised aqueous layer was extracted with dichloromethane
  4. washwashed with salt solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customthe residue purified by silica gel pressure column chromatography
  9. customThe solid residue was recrystallised from ether

Sources & evidence

ORD record
ord-20af70c701d14953a299c24e96943a4a
Source dataset
uspto-grants-1997_04
Patent number
US05622951

Reaction notes

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