Potassium Carbonate → 3-(3-Methoxyphenyl)-N1-[(4-methoxyphenyl)methyl]-N7,N7-dimethyl-1,7-isoquinolinediamine

HRID 1878640Notes

Reaction equation

HRID 1878640 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:3]=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[N:3]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 78357864HCID 78357864, compound

Product 1

HCID 692989333-(3-Methoxyphenyl)-N1-[(4-methoxyphenyl)methyl]-N7,N7-dimethyl-1,7-isoquinolinediamineYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-chloroimine isoquinoline II (500 mg, 1.6 mmol), 4-methoxy benzylamine (877 mg, 6.4 mmol), and potassium carbonate (2 g, 15 mmol) in DMF was refluxed overnight. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with water, dried, and concentrated. The residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (3:1) to afford compound III (310 mg, 47%). 1H NMR (300 MHz, CDCl3) δ: 7.74-7.62 (m, 3H), 7.45-7.33 (m, 4H), 7.22 (m, 1H), 6.92 (m, 3H), 6.66 (m, 1H), 5.24 (s, 1H), 4.91 (d, 2H), 3.91 (s, 3H), 3.85 (s, 3H), 3.09 (s, 6H).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-2a8a3ccf837c4bafa7e7c27798240244
Source dataset
uspto-grants-2012_11
Patent number
US08314123B2

Reaction notes

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