Potassium Carbonate → HCID 19974526, compound

HRID 1451659Notes

Reaction equation

HRID 1451659 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[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][NH:19][CH2:20]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:14][C:15]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][N:19]([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]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 451085,6-DimethoxytetrahydroisoquinolineHCID 792664-Nitrophenethyl bromide

Product 1

HCID 19974526HCID 19974526, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-bromoethyl)-4-nitrobenzene (0.3 g), 1,2,3,4-tetrahydro-5,6-dimethoxyisoquinoline [0.25 g; R. D. Haworth, J. Chem. Soc., 2281 (1987); Robin D. Clark, J. Med. Chem., 596-600, 33, (1990)] and potassium carbonate (0.5 g) in DMF (25 ml) was heated at 60° for 3 h. The mixture was then filtered and the filtrate evaporated. The residue was 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 (0.3 g) as an orange solid, MP:97°. NMR includes signals at d 3.6 (2H,s,N--CH2Ar), 3.75 (6H,s,OCH3).

Workup

  1. temperaturewas heated at 60° for 3 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-9e800bbd225a43b19c4aa17d8f198123
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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