HCID 67065996, compound → HCID 24904257, compound

HRID 2093147Notes

Reaction equation

HRID 2093147 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[F:22])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[F:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 67065996HCID 67065996, compound

Product 1

HCID 24904257HCID 24904257, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-4-(2-fluoro-4-methoxyphenyl)1,2,3,6-tetrahydropyridine (Step B; 117 mg; 0.393 mmol) in MeOH (10 mL) was treated with a catalytic amount of 10% Pd/C and the reaction was placed under an atmosphere of H2 (Parr Shaker; 45 PSI) for 48 h. The reaction was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient) to afford 4-(2-fluoro-4-methoxyphenyl)piperidine as a tan solid. LCMS=210.1 (M+1)+. 1 H NMR (CDCl3, 500 MHz) δ 7.16 (t, J=8.7 Hz, 1 H), 6.68 (dd, J=8.7, 2.5 Hz, 1 H). 6.60 (dd, J=12.3, 2.5 Hz, 1 H), 3.78 (s, 3 H), 3.63 (d, J=12.6 Hz, 2 H), 3.09-2.98 (m, 2 H), 2.18 (q, J=12.1 Hz, 2 H), 2.02 (d, J=13.3 Hz, 2 H).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash silica gel chromatography (0-100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-4c6b10b849f049e5b86b0fcaff90a1be
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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