1,2,3,4-Tetrahydroisoquinoline → HCID 10380803, compound

HRID 1451656Notes

Reaction equation

HRID 1451656 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[CH2:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:16]2[CH2:17][CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 2611281-(3-bromopropoxy)-4-nitrobenzene

Product 1

HCID 10380803HCID 10380803, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-bromopropoxy)-4-nitrobenzene (10 g), 1,2,3,4-tetrahydroisoquinoline (5.1 g) and potassium carbonate (10.6 g) in DMF (100 ml) was stirred at 70° for 24 h. The mixture was then filtered and the filtrate evaporated. The residue was taken up with water and extracted with dichloromethane. The organic layer was washed with water, dried, evaporated and purified by column chromatography eluting with dichloromethane/methanol (96:4) to give the title compound (8.8 g) as a yellow oil. NMR includes signals at d 3.6 (2H,s,N--CH2Ar), 4.1 (2H,t,O--CH2).

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography
  8. washeluting with dichloromethane/methanol (96:4)

Sources & evidence

ORD record
ord-34d0f8ace30a4d25bf0afd0adcc6e962
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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