ChemicalBook CAS DataBase List BIS-(4-METHOXY-BENZYL)-AMINE

BIS-(4-METHOXY-BENZYL)-AMINE synthesis

13synthesis methods

Product Name:BIS-(4-METHOXY-BENZYL)-AMINE
CAS Number:17061-62-0
Molecular formula:C16H19NO2
Molecular Weight:257.33

Bis-(4-methoxybenzyl)-amine is an amine organic compound, which can be used as a pharmaceutical intermediate for laboratory organic synthesis and chemical and pharmaceutical research and development. Synthesis of bis-(4-methoxybenzyl)-amine was prepared by reductive amination of 4-methoxybenzaldehyde and 4-methoxybenzylamine.

3261-60-7 Synthesis

N-(4-Methoxybenzylidene)-N-(4-methoxybenzyl)amine

3261-60-7
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17061-62-0
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Yield:17061-62-0 100%

Reaction Conditions:

with sodium tetrahydridoborate in methanol at 5; for 2.75 h;Heating / reflux;

Steps:

5

p-Anisaldehyde (25.0 g, 0.1836 mol), 4-methoxybenzylamine (25.3 g, 0.1836 mol) and toluene (150 mL) were combined in a 500 mL round bottom flask which was fitted with a condenser and Dean-Stark trap under a N₂ atmosphere. The solution was refluxed for 3 hours during which time 3 mL of H₂O was azeotroped away from the reaction mixture. The reaction was cooled and concentrated on a rotovap at 40⁰C for 2 hours. The clear, yellow oil was taken up in MeOH (150 mL) in a 500 mL round bottom flask fitted with a condenser under a N₂ atmosphere. The reaction was cooled to 5°C, and NaBH₄ was added in small portions over 45 min (off-gassing occurred). The reaction was slowly heated to reflux with vigorous off-gassing. After 2 hours at reflux, the reaction was cooled to room temperature and concentrated on the rotorvap at 30⁰C for 2 hours, and then placed under high vacuum at 3O⁰C for 1 hour to give the title compound as a white crystalline solid (47.13 g, quantitative yield; 98.6 % purity by HPLC). MH⁺ = 258.1

References:

WO2007/109810,2007,A2 Location in patent:Page/Page column 112

874-90-8 Synthesis