1-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-one → 1-(2-Hydroxyethyl)-5-phenylpiperidin-2-one

HRID 1878729Notes

Reaction equation

HRID 1878729 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][C:12]1=[O:23])C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[OH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH2:13][C:12]1=[O:23]

Participants

5

Reactant 2

HCID 598430561-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 598430141-(2-Hydroxyethyl)-5-phenylpiperidin-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(2-(benzyloxy)ethyl)-5-phenylpyridin-2(1 H)-one (100 mg, 327 μmol) in MeOH (10 mL) was sparged with argon for 10 min. A portion of palladium hydroxide (46 mg, 327 μmol) was added and the reaction was subjected to 55 psi hydrogen in a Parr shaker for 1 hr. The mixture was filtered through a pad of Celite, and concentrated to a white solid under reduced pressure. MS (ESI pos. ion) m/z (MH+): 220. Calc'd exact mass for C13H17NO2: 219. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.00-2.14 (m, 2 H) 2.46-2.67 (m, 2 H) 3.07-3.18 (m, 1H) 3.33 (br. s., 1 H) 3.42-3.56 (m, 3 H) 3.60-3.68 (m, 1 H) 3.83 (t, J=4.89 Hz, 2H) 7.21-7.30 (m, 3 H) 7.35 (t, J=7.24 Hz, 2 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 27.75, 31.9, 40.37, 51.24, 55.88, 61.79, 126.99, 127.30, 128.85, 141.51, 171.78.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated to a white solid under reduced pressure

Sources & evidence

ORD record
ord-655a483b698e40f0af6263e84b7f1cf5
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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