Pyridine → 2-[(N,N-Dimethylamino)methyl]-6-[4-[(2-methoxybenzoyl)amino]benzyloxy]tetralin

HRID 1242884Notes

Reaction equation

HRID 1242884 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH:30]([CH2:35][N:36]([CH3:38])[CH3:37])[CH2:29][CH2:28]3)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:38][N:36]([CH2:35][CH:30]1[CH2:29][CH2:28][C:27]2[C:32](=[CH:33][CH:34]=[C:25]([O:24][CH2:23][C:22]3[CH:21]=[CH:20][C:19]([NH:18][C:1](=[O:10])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[O:8][CH3:9])=[CH:40][CH:39]=3)[CH:26]=2)[CH2:31]1)[CH3:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 889692-Methoxybenzoyl chlorideHCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

Product 1

HCID 210630372-[(N,N-Dimethylamino)methyl]-6-[4-[(2-methoxybenzoyl)amino]benzyloxy]tetralin

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

o-Anisoyl chloride (0.15 ml) was added dropwise to pyridine solution (4 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (200 mg) under ice-cooling, which was stirred at room temperature for 30 minutes. 10% aqueous potassium carbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent; THF), and recrystallized (ethyl acetate-hexane) to give the titled compound (200 mg).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0bccfe6a22f34ba6a9e351a138113342
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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