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

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Reaction Steps

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##

Provenance & Evidence