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

HRID 2301395Notes

Reaction equation

HRID 2301395 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[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[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 7852PropylamineHCID 777857-Methoxy-2-tetraloneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 7-Methoxy-3,4-dihydro-1-H-naphthalen-2-one (5.0 g, 28.4 mmol) and propylamine (2.8 mL, 34 mmol, 1.2 eq) in 1,2-dichloroethane (150 mL) under inert atmosphere was added sodium triacetoxyborohydride (15 g, 71 mmol, 2.5 eq) in a single portion. The reaction was allowed to stir at room temperature for 20 h then concentrated in-vacuo. The residue was partitioned between 10% aq. KOH (150 mL) and ethyl acetate (75 mL). The organic layer was washed with brine, dried and concentrated. The resulting material was dissolved in diethyl ether (100 mL) and treated with 1 M HCl in ether (28.4 ML). The solid was collected and dried under vacuum to afford 6.23 g of (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl-propyl-amine as hydrochloride salt.

Workup

  1. concentrationthen concentrated in-vacuo
  2. customThe residue was partitioned between 10% aq. KOH (150 mL) and ethyl acetate (75 mL)
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe resulting material was dissolved in diethyl ether (100 mL)
  7. additiontreated with 1 M HCl in ether (28.4 ML)
  8. customThe solid was collected
  9. customdried under vacuum

Sources & evidence

ORD record
ord-ef107def5ad74f1c91aec4561d618c89
Source dataset
uspto-grants-2002_12
Patent number
US06500822B2

Reaction notes

Loading…