ChemicalBook CAS DataBase List 4-Aminobenzylamine

4-Aminobenzylamine synthesis

12synthesis methods

Product Name:4-Aminobenzylamine
CAS Number:4403-71-8
Molecular formula:C7H10N2
Molecular Weight:122.17

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Yield:4403-71-8 72%

Reaction Conditions:

with methanol;sodium tetrahydroborate;nickel(II) chloride hexahydrate at 20; for 0.25 h;chemoselective reaction;

Steps:

General procedure
General procedure: In a typical experiment, benzyl 4-methoxyphenyl carbamate (1a, 1 mmol) and 10 cm³ methanol were placed in a 100 cm³ round-bottomed flask fitted with a water condenser and placed over a magnetic stirrer. Nickel(II) chloride hexahydrate (5 mmol) was added to the flask, followed by slow addition of sodium borohydride (15 mmol) with vigorous stirring. A vigorous reaction took place and the reaction mixture turned black due to in situ formation of nickel boride. The progress of the reaction was monitored by TLC (petroleum ether: ethyl acetate 80:20, v/v). After completion, the reaction mixture was filtered through a Celite pad (~2.5 cm) and washed with methanol (3x10 cm³). The solution was concentrated ona rotavapor and diluted with water (~50 cm³), followed by extraction with dichloromethane (3x10 cm³). The combined dichloromethane extract was washed with water and dried over anhyd. K₂CO₃. The solvent was removed ona rotary evaporator and the product was dried. 4-Anisidine(2a) was obtained as colourless solid in 88% yield. The products were identified by m.p., IR, and NMR spectra. The products Scheme 1, entry 24 and Scheme 2, entry 8 were purified by flash column chromatography on silica gel using petroleum ether:ethyl acetate (95:5, v/v) as eluent.

References:

Saroha, Mohit;Aggarwal, Komal;Bartwal, Gaurav;Khurana, Jitender M. [Monatshefte fur Chemie,2018,vol. 149,# 12,p. 2231 - 2235]

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