Sodium Bicarbonate → 2-(4,4-Diphenylbutyl)-1,2,3,4-tetrahydroisoquinolin-5-ol

HRID 963981Notes

Reaction equation

HRID 963981 reaction equation
[Br-].[C:2]1([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][CH2:10][CH2:11][N+:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[OH:22])[CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].C(=O)(O)[O-].[Na+]>CO.[Pd]>[C:23]1([CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([OH:22])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 158708932-(4,4-Diphenylbutyl)-5-hydroxyisoquinolinium bromideHCID 178418361HCID 178418361, compound

Product 1

HCID 158708902-(4,4-Diphenylbutyl)-1,2,3,4-tetrahydroisoquinolin-5-olYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4,4-diphenylbutyl)-5-hydroxyisoquinolinium bromide (2.29 g, 5.27 mmol) in 100 mL of methanol was added 20% Pd/C catalyst (0.7 g). The reaction mixture was shaken under 50 psi of hydrogen at room temperature for 18 hours. The catalyst was then removed by filtration through a pad of Celite. The residue was washed with methanol, and the filtrate was concentrated under vacuum. The white solid obtained was neutralized with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (2×200 mL). The organic extracts were collected and dried with magnesium sulphate, filtered and concentrated to give 1.9 g of crude product as a yellow oil.

Workup

  1. customThe catalyst was then removed by filtration through a pad of Celite
  2. washThe residue was washed with methanol
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe white solid obtained
  5. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  6. customThe organic extracts were collected
  7. dry with materialdried with magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-48188ee99a2144ce963743c2de981de4
Source dataset
uspto-grants-1998_06
Patent number
US05767129

Reaction notes

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