Potassium Carbonate → HCID 10361909, compound

HRID 1451632Notes

Reaction equation

HRID 1451632 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.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][NH:23][CH2:22][CH2:21]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][N:23]([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)[CH2:22][CH2:21]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2611281-(3-bromopropoxy)-4-nitrobenzeneHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 10361909HCID 10361909, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-bromopropoxy)-4-nitrobenzene (10 g), 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride (8.8 g) and potassium carbonate (10.6 g) in DMF (100 ml) was heated at 100° for 16 h. The mixture was then filtered and the filtrate evaporated. The 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 ether to give the title compound (11.3 g), m.p. 100°.

Workup

  1. temperaturewas heated at 100° for 16 h
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  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 ether

Sources & evidence

ORD record
ord-ca46219a13b54da39dd6280e340590a1
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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