5-(Diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]pyridin-2(1H)-one → 5-(Diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]piperidin-2-one

HRID 2389351Notes

Reaction equation

HRID 2389351 reaction equation
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:24])[N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.O=[Pt]=O>[C:25]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]2[CH2:13][N:12]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[C:11](=[O:24])[CH2:10][CH2:9]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 685374545-(Diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]pyridin-2(1H)-one

Product 1

HCID 685380155-(Diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]piperidin-2-oneYield 54.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

5-(Diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]pyridin-2(1H)-one (1 g) in EtOH (20 mL) was added dioxoplatinum (70 mg) at ambient temperature and the mixture was stirred at ambient temperature for 1 day under hydrogen atmosphere. The mixture was filtered through a bed of celite. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:3) to afford 5-(diphenylmethyl)-1-[3-(3-hydroxyphenyl)propyl]piperidin-2-one (550 mg) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=1:3)

Sources & evidence

ORD record
ord-f04ac8fe34ea462998bcea677d3d40be
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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