ChemicalBook CAS DataBase List BENZYL-(4-FLUORO-BENZYL)-AMINE

BENZYL-(4-FLUORO-BENZYL)-AMINE synthesis

13synthesis methods

Product Name:BENZYL-(4-FLUORO-BENZYL)-AMINE
CAS Number:55096-88-3
Molecular formula:C14H14FN
Molecular Weight:215.27

Benzenemethanamine, N-[(4-fluorophenyl)methylene]-

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55096-88-3
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Yield:55096-88-3 90%

Reaction Conditions:

with magnesium;pinacolborane;iron(II) chloride in tetrahydrofuran at 60; for 12 h;Inert atmosphere;Schlenk technique;

Steps:

General Procedure for Reduction of Imine

General procedure: To a 15 mL Schlenk tube containing a magnetic stir bar, was added imine (0.5 mmol), FeCl₂ (3 mg, 5 mol%) and Mg (1 mg, 0.05 mmol). Then HBpin (87 mL, 0.6 mmol) and a freshly distilled THF (2 mL) were added respectively by a syringe under atmosphere of nitrogen. The mixture was stirred in a pre-heated oil bath at 60 °C for 12 h under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 20:1 to 3:1) to afford secondary amine.

References:

Lei, Siyu;Pan, Tao;Wang, Maorong;Zhang, Yuexia [Tetrahedron Letters,2022,vol. 102,art. no. 153949] Location in patent:supporting information

459-57-4 Synthesis