Potassium Carbonate → HCID 19974504, compound

HRID 1451658Notes

Reaction equation

HRID 1451658 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[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+]>CN(C=O)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][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5916183-Nitrophenethyl bromideHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 19974504HCID 19974504, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-bromoethyl)-3-nitrobenzene (2.3 g), 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride (2.3 g) and potassium carbonate (3 g) in DMF (50 ml) was heated at 50° for 12 h. The mixture was then filtered and the filtrate evaporated. The residue was then taken up in water, extracted with dichloromethane, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (99:1) to give the title compound (1.4 g) as a yellow oil. NMR includes signals at d 3.6 (2H,s,N--CH2Ar), 3.75 (6H,s,OCH3).

Workup

  1. temperaturewas heated at 50° for 12 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (99:1)

Sources & evidence

ORD record
ord-f7e030bc0b8d4cc5be3bf6e0961e3fba
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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