Aluminium lithium hydride → 2-[Phenethylaminomethyl]-1,2,3,4-tetrahydronaphthalene

HRID 1720968Notes

Reaction equation

HRID 1720968 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]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53953585N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amide

Product 1

HCID 115798362-[Phenethylaminomethyl]-1,2,3,4-tetrahydronaphthaleneYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. temperatureThe mixture was refluxed for 4 hrs
  2. customthen carefully quenched by addition of solid Na2SO4 ·10H2O
  3. customthe solid was removed by filtration and concentration of filtrate in vacuo

Sources & evidence

ORD record
ord-21a8b123a5a24a6b8926d13d42831234
Source dataset
uspto-grants-1996_04
Patent number
US05508306

Reaction notes

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