HCID 13755070, compound → 3-(4-Methoxyphenyl)piperidine

HRID 1507185Notes

Reaction equation

HRID 1507185 reaction equation
C([N:8]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:13]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 13755070HCID 13755070, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 129379203-(4-Methoxyphenyl)piperidineYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-5-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1.5 g, 5.4 mmol) in 50 mL of methanol was added 10% Pd/C (1.14 g). Hydrogen gas was introduced via balloon and the reaction mixture was stirred overnight at rt. The reaction mixture was then filtered through Celite, and the filter pad was washed with additional methanol (100 mL). The filtrates were combined, and the methanol was evaporated under reduced pressure to give 3-(4-methoxyphenyl)piperidine (950 mg, 3.73 mmol, 69.4% yield). LCMS (Method 107): (ES-API), m/z 192.2 (M+H) RT=1.497 min; 1H NMR (300 MHz, DMSO-d6) δ 7.13 (dt, J=8.5, 2.0 Hz, 2H), 6.84 (dt, J=8.5, 2.2 Hz, 2H), 3.72 (s, 3H), 3.17 (s, 2H), 2.93 (d, J=10.6 Hz, 2H), 2.49-2.39 (m, 1H), 1.81 (d, J=1.9 Hz, 1H), 1.74-1.57 (m, 1H), 1.57-1.40 (m, 2H).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe filter pad was washed with additional methanol (100 mL)
  3. customthe methanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-343bda5298a24223bce1865455728fb5
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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