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

HRID 1741705Notes

Reaction equation

HRID 1741705 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 KI. 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-c74838b2ce714eeea8ee9ac081d9cd28
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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