Benzylamine → HCID 178500968, compound

HRID 1530812Notes

Reaction equation

HRID 1530812 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H][H]>CO.[Pd]>[CH2:17]([NH:24][C@@H:2]1[CH2:7][CH2:6][C@H:5]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])[CH2:4][CH2:3]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 46238246Dimethyl (4-oxocyclohexyl)malonateHCID 178418361HCID 178418361, compound

Product 1

HCID 178500968HCID 178500968, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

34.0 g of dimethyl (4-oxocyclohexyl)malonate and 16.1 g of benzylamine in 200 ml of methanol were reacted at 65° C. and 5 bar hydrogen pressure in the presence of 5 g of palladium/carbon catalyst (5%). The catalyst was filtered off and the mixture was concentrated. The cis/trans isomers were separated by silica gel chromatography (ethyl acetate/methanol 19:1).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe mixture was concentrated
  3. customThe cis/trans isomers were separated by silica gel chromatography (ethyl acetate/methanol 19:1)

Sources & evidence

ORD record
ord-5b76d2cedb2a4a25a30cbafbc22a3183
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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