Acetonitrile → HCID 20445312, compound
Reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:23](#[N:25])[CH3:24]>>[NH2:25][CH:23]([C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH3:24]Participants
Procedure
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.
Workup
- custommay be obtained
Sources & evidence
- ORD record
- ord-32c5a58b447c40d5bc16b65710348fc3
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04473586
Reaction notes
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