(+/-)-Benzyl 3-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate → (+/-)-6-Methoxy-2-methyl-4-phenyl-3-piperidin-3-ylisoquinolin-1(2H)-one

HRID 17867Notes

Reaction equation

HRID 17867 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16]1)=[C:6]2[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]1)=[C:6]2[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 1

HCID 11397523(+/-)-Benzyl 3-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 11279492(+/-)-6-Methoxy-2-methyl-4-phenyl-3-piperidin-3-ylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an ethanol (15 mL) solution of (±)-benzyl 3-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate (201 mg, 0.417 mmol) in a Parr hydrogenation jar was added 10% palladium on carbon catalyst (50 mg). The contents of the jar were hydrogenated at 60 psi for four hours. Filtration through celite followed by evaporation of the filtrate in vacuo gave the titled product as a white foam. Proton NMR for the product was consistent with the titled compound. ESI+MS: 349.2 [M+H]+.

Workup

  1. filtrationFiltration through celite
  2. customfollowed by evaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-313a79d6c98346518fee81bb1b92a5c2
Source dataset
uspto-grants-2010_06
Patent number
US07741322B2

Reaction notes

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