Acetonitrile → HCID 20445312, compound

Participants

Reaction Steps

As set forth in the foregoing reaction scheme, the 1-aminoalkyl-3,4-dihydronaphthalene compounds of the invention wherein n is 1 are obtained by reacting a 1,2,3,4-tetrahydro-1-naphthalenone with, for example, trimethylsilylcyanide in the presence of a catalytic amount of, for example, aluminum trichloride followed by reduction with lithium aluminum hydride to obtain the corresponding 1-aminomethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene. Similarly, the compounds of the invention wherein n is 2 may be obtained by reacting a 1,2,3,4-tetrahydro-1-naphthalenone with, for example, acetonitrile and n-butyl lithium, followed by reduction with lithium aluminum hydride to obtain the corresponding 1-aminoethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene. The 1-aminoalkyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene intermediate is then subjected to acid dehydration to obtain the corresponding 1-aminoalkyl-3,4-dihydronaphthalene compound.

Provenance & Evidence