Aluminium lithium hydride → 2-[Phenethylaminomethyl]-1,2,3,4-tetrahydronaphthalene
Reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:8]([NH:9][CH2:10][CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Procedure
The solution of N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amide (693 mg, 2.48 mmol) in 15 ml of THF was treated with LiAlH4 (149 mg, 3.72 mmol). The mixture was refluxed for 4 hrs then carefully quenched by addition of solid Na2SO4 ·10H2O. After stirred at r.t. overnight, the solid was removed by filtration and concentration of filtrate in vacuo gave a colorless oil (604 mg, 91.7%). The product was converted to HCl salt, crystallization with MeOH/Et2O gave a white powder; mp 260°-263° C.; Calcd for C19H23N·HCl: C 75.58, H 8.03, N 4.64: Found: C 75.77, H, 8.24, N 4.45.