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

HRID 479357Notes

Reaction equation

HRID 479357 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 (1 50 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 20h 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 1M 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 1M HCl in ether (28.4 ML)
  8. customThe solid was collected
  9. customdried under vacuum

Sources & evidence

ORD record
ord-709249d46d9e449887a8e8259216002b
Source dataset
uspto-grants-2003_11
Patent number
US06645958B2

Reaction notes

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