Hydrochloric Acid → 1-Aminomethyl-3,4-dihydronaphthalene

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Reaction Steps

1-Aminomethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene, the product of Example 7, was refluxed in a 2N solution of hydrogen chloride in 2-propanol (250 mL) for 5 hours. A portion of the 2-propanol was removed under reduced pressure to give a slurry. Diethyl ether was added to precipitate the hydrochloride salt. The resulting suspension was then filtered. The filter cake was then recrystallized from methanol/diethyl ether to give 16.18 g (59% yield based on 1,2,3,4-tetrahydronaphthalene-1-one) of the desired product as a light tan solid; 1H NMR (CD3OD) δ 2.31-2.40 (m, 2H), 2.80 (t, 2H, J=8 Hz), 4.0 (s, 2H), 6.26 (t, 1H, J=4.5 Hz), 7.19-7.29 (m, 4H).

Provenance & Evidence