Acetic Acid → 7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 2294754Notes

Reaction equation

HRID 2294754 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:14]([NH2:17])[CH2:15][CH3:16].C(O)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:17][CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7852PropylamineHCID 777857-Methoxy-2-tetralone

Product 1

HCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-methoxy-2-tetralone (32 mmol. 5 g), n-propylamine (60 mmol. 5 mL), acetic acid (60 mmol. 4 mL), molecular sieves 3A (5 g) in ethanol (25 mL) was stirred at room temperature for 2.5 hrs. The solution was filtered on paper in a Paar bottle and the reduction was carried out with PtO2 (100 mg) as the catalyst, under 30 PSI of hydrogen. When the pressure dropped to 6 PSI (30 min.), the catalyst was removed by elution onto a column (celite 545) with chloroform. The eluent was concentrated under vacuum. The residue, a brown oil, was converted to solid by formation of hydrogen chloride salt in ether/HCl. Several recrystallizations in ether/methanol (60/40) afforded the final product (1) as white crystals (4.28 g, 61% yield).

Workup

  1. filtrationThe solution was filtered on paper in a Paar bottle
  2. additionWhen the pressure dropped to 6 PSI (30 min.)
  3. customthe catalyst was removed by elution onto a column (celite 545) with chloroform
  4. concentrationThe eluent was concentrated under vacuum
  5. customSeveral recrystallizations in ether/methanol (60/40)

Sources & evidence

ORD record
ord-abeb444334c448739562e8698a722939
Source dataset
uspto-grants-1997_11
Patent number
US05690906

Reaction notes

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