Acetic Acid → 6-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

HRID 1242897Notes

Reaction equation

HRID 1242897 reaction equation
C(O)(=O)C.[CH3:5][N:6]([CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH:15]=2)[CH2:10]1)[CH3:7]>[Zn].C1COCC1>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH:9]([CH2:8][N:6]([CH3:5])[CH3:7])[CH2:18][CH2:17]3)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 219399852-[(N,N-Dimethylamino)methyl]-6-(4-nitrobenzyloxy)tetralin

Product 1

HCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralinYield 60.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After acetic acid (6 ml) was added to THF solution (12 ml) of 2-[(N,N-dimethylamino)methyl]-6-(4-nitrobenzyloxy)tetralin (1.91 g) under ice-cooling, zinc powder (3.67 g) was further added, which was stirred for 6 hours. The reaction mixture was filtered, and the filtrate was concentrated. 10% aqueous potassium carbonate solution and ethyl acetate were added to the residue, the precipitate was removed by celite filtration, and the filtrate was extracted 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 aluminum column chromatography (development solvent; hexane˜hexane:ethyl acetate=4:1) to give the titled compound (1.05 g).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. addition10% aqueous potassium carbonate solution and ethyl acetate were added to the residue
  5. customthe precipitate was removed by celite filtration
  6. extractionthe filtrate was extracted
  7. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified

Sources & evidence

ORD record
ord-0b9b7bdcb5654caa9f4dea24de194d8b
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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