Hydrochloric Acid → N-Methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methyl-1,3-propanediamine

HRID 1769660Notes

Reaction equation

HRID 1769660 reaction equation
[CH3:1][N:2]([CH2:15][CH:16]([CH3:19])[C:17]#[N:18])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.Cl>C(O)C.[Pt]=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[CH2:15][CH:16]([CH3:19])[CH2:17][NH2:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 199703153-[N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)amino]-2-methylpropionitrile

Product 1

HCID 15045284N-Methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methyl-1,3-propanediamineYield 92.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

2.1 g of the above nitrile and 0.2 ml of concentrated hydrochloric acid were dissolved in 30 ml of ethanol, followed by the addition of 0.2 g of platinum oxide to carry out hydrogenation under a hydrogen pressure of 2.1 kg/cm2. The reaction mixture was filtered to remove the catalyst. The filtrate was distilled under a reduced pressure to remove the ethanol. The residue was made alkaline with a dilute solution of caustic soda. The aqueous layer was extracted with dichloromethane. The extract was washed with water, dried over magnesium sulfate and distilled under a reduced pressure to obtain 1.98 g of the title compound as a pale yellow oil (yield: 38%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. distillationThe filtrate was distilled under a reduced pressure
  4. customto remove the ethanol
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-e265f410f1c1482cb453ef1c730b44b9
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

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