6,7-Dimethoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine → HCID 4101513, compound

HRID 728056Notes

Reaction equation

HRID 728056 reaction equation
C(N[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH3:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)CC.CC1C=CC(C(O)C(OC(=O)C)=O)=CC=1>CC(C)=O>[CH3:18][O:17][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[O:15][CH3:16])[CH2:13][CH2:14][CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 123816206,7-Dimethoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 88496009HCID 88496009, compound

Product 1

HCID 4101513HCID 4101513, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(N-propyl)amino-6,7-dimethoxy tetraline (3.69 g; 0.0147 moles) (prepared as indicated in step (a) of Example 2 was dissolved in 43 cc of acetone. To the resulting solution the acid chloride of p-methyl-O-acetyl-mandelic acid (1.45 g; 0.007 moles) was added. The solution was kept at room temperature for 30 minutes and subsequently filtered and concentrated under vacuum. The residue was taken up with methylene chloride and washed with 5% HCl, 5% NaHCO3 and H2O to neutrality. The organic phase was dried over anhydrous Na2SO4 and brought to dryness. 2.4 g of 2-[(N-propyl, N-p-methyl-O-acetyl mandelyl)amino]-6,7-dimethoxy tetraline were obtained. To the amide thus obtained (2.4 g; 0.0058 moles) BH3 in THF (17.4 cc; 0.017 moles) was added at 0° C. The solution was kept at the reflux temperature for three hours. Subsequently, 16 cc of 6N HCl were added at 0° C., the solution was kept at the reflux temperature for 30 minutes and then concentrated under vacuum in order to remove the THF. The acid solution was alkalinized with 4N NaOH and extracted with chlorophorm. The organic phase was washed with H2O to neutrality and concentrated under vacuum. The solid which formed was taken up with ethyl acetate and upon addition of gaseous HCl 1.4 grams of a white solid product were obtained (yield 74%). ##STR28##

Workup

  1. filtrationsubsequently filtered
  2. concentrationconcentrated under vacuum
  3. washwashed with 5% HCl, 5% NaHCO3 and H2O to neutrality
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-40048bb37fd34dfcac60f4954d05accf
Source dataset
uspto-grants-1991_09
Patent number
US05047433

Reaction notes

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