Cesium carbonate → 6-(2-Methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257049Notes

Reaction equation

HRID 257049 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:5]2.Cl[CH2:23][C:24]([CH3:26])=[CH2:25].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:25][C:24](=[CH2:23])[CH2:26][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 112413-Chloro-2-methyl-1-propeneHCID 189639836-Hydroxy-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 189639656-(2-Methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-hydroxy-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline (1.5 g, 5.34 mmol) in acetone (80 ml) is added 3-chloro-2-methylpropene (8 ml, 8.01 mmol), Cs2CO3 and a catalytic amount of Kl. The reaction is then refluxed for 24 hours. After this time the reaction mixture is cooled to ambient temperature and filtered. The filter cake is washed with acetone (3×50 ml) and the combined organics concentrated in vacuo. The residue is chromatographed (silica gel, 1:4 EtOAc/hexane) to give 6-(2-methyl-2-propenyloxy)-2-(3-phenylpropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. temperatureThe reaction is then refluxed for 24 hours
  2. filtrationfiltered
  3. washThe filter cake is washed with acetone (3×50 ml)
  4. concentrationthe combined organics concentrated in vacuo
  5. customThe residue is chromatographed (silica gel, 1:4 EtOAc/hexane)

Sources & evidence

ORD record
ord-247d81c7b7a74d9c86d323f2402e4970
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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