Bis(2-Methoxyethyl)amine → 1,2,3,4-Tetrahydro-8-methoxy-N,N-bis(2-methoxyethyl)-2-naphthalenamine

HRID 1078071

Reaction equation

HRID 1078071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[CH2:10][CH2:9][CH2:8]2.[CH3:14][O:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][O:21][CH3:22]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:18]([CH2:19][CH2:20][O:21][CH3:22])[CH2:17][CH2:16][O:15][CH3:14])[CH2:9][CH2:8]2

Participants

5

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 112753358-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 183318041,2,3,4-Tetrahydro-8-methoxy-N,N-bis(2-methoxyethyl)-2-naphthalenamineYield 80%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1.76 g (10 mmol) 8-methoxy tetralone, 2.66 g (20 mmol) N,N-bis(-2methoxyethyl)amine, and 25 mg p-toluenesulfonic acid in toluene was heated to reflux under a N2 atmosphere. The flask was equipped with a Dean-Stark trap to collect H2O. TLC analysis was used to monitor the reaction. After 48 hours, the solvent was removed in vacuo. The crude ene-amine was hydrogenated using 450 mg 10% pd/C in 50 mL MeOH at 50 psi H2 for 24 hours. The reaction mixture was filtered over celite and the filtrate purified by liquid chromatography on 400 g of silica gel-60 (230-400 mesh), eluting with hexane/ethyl acetate/isopropanol (10:5:1). Fractions homogeneous by TLC were combined and concentrated in vacuo to give pure title compound as a yellow oil (2.3 g, 80%).

Workup

  1. temperatureto reflux under a N2 atmosphere
  2. customThe flask was equipped with a Dean-Stark trap
  3. customto collect H2O
  4. customthe reaction
  5. customthe solvent was removed in vacuo
  6. waitpd/C in 50 mL MeOH at 50 psi H2 for 24 hours
  7. filtrationThe reaction mixture was filtered over celite
  8. customthe filtrate purified by liquid chromatography on 400 g of silica gel-60 (230-400 mesh)
  9. washeluting with hexane/ethyl acetate/isopropanol (10:5:1)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd3701025fd141bbb1cf73490c632a8e
Source dataset
uspto-grants-1996_08
Patent number
US05545755

Linked notes

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