BIS(4-METHOXYBENZYL)AMINE HCL SALT Chemical Properties

Melting point:

243-245 °C

storage temp. 

Inert atmosphere,Room Temperature

Appearance

White to off-white Solid

InChI

InChI=1S/C16H19NO2.ClH/c1-18-15-7-3-13(4-8-15)11-17-12-14-5-9-16(19-2)10-6-14;/h3-10,17H,11-12H2,1-2H3;1H

InChIKey

BZIDDCTZNYMKMG-UHFFFAOYSA-N

SMILES

N(CC1=CC=C(OC)C=C1)CC1C=CC(OC)=CC=1.Cl

BIS(4-METHOXYBENZYL)AMINE HCL SALT Usage And Synthesis

Synthesis

Preparation of Intermediate 1-16: p-Methoxybenzaldehyde (1.8 mL, 14.8 mmol) was mixed with 4-methoxybenzylamine (1.9 mL, 14.8 mmol) in 50 mL of ethanol and the reaction was carried out at reflux for 4 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and sodium borohydride (562 mg, 14.8 mmol) was slowly added followed by stirring at room temperature for 18 hours. After cooling to 0 °C again, 50 mL of water and 250 mL of dichloromethane were added to separate the organic phase. The aqueous layer was further extracted with dichloromethane (2 x 250 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved in 100 mL of ether, cooled to 0 °C, and about 10 mL of a dioxane solution of 4N HCl was added slowly and stirred at 0 °C for 2 hours. The resulting white solid was collected by filtration and washed with ether/ethyl acetate to afford the target product bis-(4-methoxybenzyl)-amine hydrochloride (3.99 g, 91% yield). The product was characterized by 1H NMR (300 MHz, DMSO): δ 9.40 (s, 2H), 7.45 (d, J=8.7 Hz, 4H), 6.98 (d, J=8.7 Hz, 4H), 4.03 (s, 4H), 3.77 (s, 6H).

References

[1] Patent: WO2011/141713, 2011, A1. Location in patent: Page/Page column 88
[2] Patent: US2013/131057, 2013, A1. Location in patent: Paragraph 0278; 0279; 0280

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