Potassium Carbonate → 6,7-Dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

HRID 1451661Notes

Reaction equation

HRID 1451661 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.Cl.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[CH2:22][NH:21][CH2:20][CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[CH2:22][N:21]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 104274766,7-Dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinolineYield 71.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (9.64 g), 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride (10.59 g) and potassium carbonate (17.38 g) in isopropanol (150 ml) was refluxed for 48 h. The mixture was then filtered and the filtrate evaporated to dryness. The resulting residue was taken up in water and extracted with dichloromethane. The organic layer was washed with water, dried and evaporated to give an oil which crystallised in a mixture of 2-propanol and diethyl ether to give the title compound (10.27 g). M.p.: 118°-119°.

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated to dryness
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customcrystallised in a mixture of 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-a9f5f061a1b64884baea93d77ef3f6bb
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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