Potassium Iodide → (3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1462977Notes

Reaction equation

HRID 1462977 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16](OC)=[C:15]([OH:21])[CH:14]=2)=[CH:4][C:3]=1[O:22][CH3:23].[C:24](=[O:27])(O)[O-].[Na+].Cl[CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33].[I-].[K+]>C(O)C>[OH:21][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:27][CH3:24])[CH2:12][CH:9]1[C:10]2[C:5](=[CH:4][C:3]([O:22][CH3:23])=[CH:2][CH:11]=2)[CH2:6][CH2:7][N:8]1[CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 104291-Chloro-3-methyl-2-buteneHCID 44376613168-51-9HCID 516892Sodium Bicarbonate

Product 1

HCID 20452307(3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.38 g. (4.37 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline in 25 ml. anhydrous ethanol is mixed with 0.9 g. (10.7 mmol) sodium bicarbonate, 0.44 g. (4.2 mmol) 1-chloro-3-methylbut-2-ene and 100 mg. potassium iodide. The reaction mixture is allowed to react for 1 hour at ambient temperature and for 4 hours at 80° C. The usual working up and chromatographic purification on silica gel with chloroform as elution agent gives (3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline in the form of a yellowish foam.

Workup

  1. customto react for 1 hour at ambient temperature and for 4 hours at 80° C
  2. customchromatographic purification on silica gel with chloroform
  3. washas elution agent

Sources & evidence

ORD record
ord-26d2166143104a1d8d139904ae0aad14
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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