Tetrahydrofuran → 2-(2-Naphthyl)ethyl-amine

HRID 1371850Notes

Reaction equation

HRID 1371850 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].O1CCCC1.CCOC(C)=O>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 820082-Naphthylacetonitrile

Product 1

HCID 37843782-(2-Naphthyl)ethyl-amine

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

Combine naphth-2-ylacetonitrile (1.0 g, 6.0 mmol) and nickel(II) chloride hexahydrate (0.7 g, 3.0 mmol) and tetrahydrofuran (30 ml). Add dropwise borane-tetrahydrofuran complex, 1M solution in tetrahydrofuran (24.0 ml, 24.0 mmol). After 1 hour, evaporate to give a residue. Chromatograph on silica gel eluting with 8:2 EtOAc:MeOH+2% NH4OH) to give the title compound.

Workup

  1. customevaporate
  2. customto give a residue

Sources & evidence

ORD record
ord-8da498db5ffc41a08f5cbba0f86464a7
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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