Potassium Carbonate → 1,2,3,4-Tetrahydro-7-methoxy-2-[2-(4-nitrophenyl)ethyl]isoquinoline

HRID 1451657

Reaction equation

HRID 1451657 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.[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][NH:21][CH2:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH2:19][CH2:20][N:21]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=3)[CH2:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 4172887-Methoxy-1,2,3,4-Tetrahydroisoquinoline

Product 1

HCID 199745591,2,3,4-Tetrahydro-7-methoxy-2-[2-(4-nitrophenyl)ethyl]isoquinolineYield 31.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (3.7 g), 1,2,3,4-tetrahydro-7-methoxyisoquinoline (2.7 g; Daniel J. Sall and Gary L. Grunewald, J. Med. Chem. 1987, 30, 2208-2216) and potassium carbonate (6.7 g) in isopropanol (150 ml) was stirred under reflux for 48 h. The mixture was evaporated to dryness, and the residue was extracted with dichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was then purified by column chromatography elating with dichloromethane/methanol (99:1) to give the title compound (1.6 g) as an orange solid, MP: 92°-94°. NMR includes signals at d 3.6 (2H,m,N--CH2Ar), 3.7 (3H,s,OCH3).

Workup

  1. temperatureunder reflux for 48 h
  2. customThe mixture was evaporated to dryness
  3. extractionthe residue was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-54cde512ca574c9ea3ec4cc684c3ba64
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Linked notes

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