Pyridine → 6-[4-(Benzoylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralin

HRID 1242882Notes

Reaction equation

HRID 1242882 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[NH2:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:36])[CH3:35])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:1]([NH:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:35])[CH3:36])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

Product 1

HCID 219400636-[4-(Benzoylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralin

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzoyl chloride (0.14 ml) was added dropwise to pyridine solution (6 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (300 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; ethyl acetate), and recrystallized (THF-IPE) to give the titled compound (240 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 (THF-IPE)

Sources & evidence

ORD record
ord-63d0d8c3e3d44980a5c951e2d9e98fe4
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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