HCID 2960505, compound → Bis(4-fluorophenyl)(piperidin-4-yl)methanol

HRID 1667096Notes

Reaction equation

HRID 1667096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1>C(O)(=O)C.[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 2960505HCID 2960505, compound

Product 1

HCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

The above bis(4-fluorophenyl)(pyridin-4-yl)methanol (0.73 g, 2.45 mmol) was hydrogenated (60 pounds per square inch) in the presence of platinum oxide (0.1 g) catalyst in acetic acid (15 mL) for 6 hours at room temperature. The reaction mixture was filtered and concentrated. The concentrated filtrate was diluted with ice/water (20 mL) and neutralized with 10% aqueous sodium carbonate. The title product was collected by filtration. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.46-7.54 (m, 4H), 7.051-7.13 (m, 4H), 5.35-5.45 (bs, 1H), 2.87-2.97 (d, J=6.2 Hz, 2H), 2.45-2.56 (m, 3H), 1.24-1.38 (m, 2H), 1.16-1.22 (m, 2H); MS (DCI/NH3) m/z 304 (M+H)+.

Workup

  1. customfor 6 hours
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. additionThe concentrated filtrate was diluted with ice/water (20 mL)
  6. filtrationThe title product was collected by filtration

Sources & evidence

ORD record
ord-ae2b2dff83f34c198feed86d8c592b48
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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