Cyclopentanone → N-Cyclopentyl-N'-methyl-N'-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-propanediamin

HRID 1769657Notes

Reaction equation

HRID 1769657 reaction equation
[CH3:1][N:2]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:3][CH2:4][CH2:5][NH2:6].[C:19]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C.[Pt]=O>[CH:19]1([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 8452CyclopentanoneHCID 104449491,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

Product 1

HCID 15045280N-Cyclopentyl-N'-methyl-N'-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-propanediaminYield 100%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

500 mg of N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-propanediamine and 0.21 ml of cyclopentanone were dissolved in 5 ml of ethanol, followed by the addition of 10 mg of platinum oxide to carry out hydrogenation at a room temperature under 1 atm for 6 hours. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under a reduced pressure to obtain 660 mg of the title compound as a yellow oil (yield: 100%).

Workup

  1. customat a room temperature
  2. customfor 6 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-8d36f01d9088458bb0a7700e6ddaad51
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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