BIS(4-METHOXYBENZYL)AMINE HCL SALT

BIS(4-METHOXYBENZYL)AMINE HCL SALT Property

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

BIS(4-METHOXYBENZYL)AMINE HCL SALT Chemical Properties,Usage,Production

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