Ethanol → HCID 67538442, compound

HRID 2383043Notes

Reaction equation

HRID 2383043 reaction equation
[ClH:1].Br[C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH:8]2[CH:15]([CH3:17])[CH3:16].CCO>[Pd].C(N(CC)CC)C>[ClH:1].[CH:15]([CH:8]1[C:9]2[C:4](=[CH:3][CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:5][CH2:6][NH:7]1)([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 53494239HCID 53494239, compound

Product 1

HCID 67538442HCID 67538442, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To 5-bromo-1-isopropyl-8-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.0 g) were added EtOH (30 mL), triethylamine (1.3 mL), and 10% palladium-supported carbon (0.30 g), followed by stirring under a hydrogen atmosphere for 2 hours. The reaction liquid was filtered through celite and the solvent was evaporated. An aqueous 1 M NaOH solution was added to the reaction liquid, followed by extraction with EtOAc. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was dissolved in EtOAc (30 mL). 4 M HCl/EtOAc (5 mL) was added to the mixture, and the precipitated solid was collected to obtain 1-isopropyl-8-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.2 g).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through celite
  3. customthe solvent was evaporated
  4. additionAn aqueous 1 M NaOH solution was added to the reaction liquid
  5. extractionfollowed by extraction with EtOAc
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. dissolutionthe resulting residue was dissolved in EtOAc (30 mL)
  10. addition4 M HCl/EtOAc (5 mL) was added to the mixture
  11. customthe precipitated solid was collected

Sources & evidence

ORD record
ord-76c999b9f10a490dbc078eeac649b98c
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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