(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Chemical Properties

Melting point:

>216°C (dec.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)

form 

Solid

color 

White to Off-White

InChI

InChI=1/C12H17NO2.ClH/c1-13-7-9-4-8-5-11(14-2)12(15-3)6-10(8)9;/h5-6,9,13H,4,7H2,1-3H3;1H/t9-;/s3

InChIKey

SWSAIQSQSDOONK-OVMXBOEKNA-N

SMILES

COC1=CC2[C@@H](CNC)CC=2C=C1OC.Cl |&1:5,r|

CAS DataBase Reference

866783-13-3(CAS DataBase Reference)

Safety Information

HS Code 

29214990

(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Usage And Synthesis

Uses

(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride is an intermediate used in preparation of Ivabradine (I940500) which is a selective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node.

Uses

(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane is an intermediate used in preparation of Ivabradine (I940500) which is a selective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node.

Synthesis

The general procedure for the synthesis of (1S)-4,5-dimethoxy-1-methylaminomethyl-benzocyclobutane hydrochloride from (S)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)-N-methylmethylamine is as follows: (1S)-4,5-dimethoxy-1-methylaminomethyl-benzocyclobutane hydrochloride, which was obtained from the previous step, was was dissolved in a solvent mixture of ethyl acetate (20 mL) and ethanol (5 mL) and stirred at 20 °C. Subsequently, hydrogen chloride gas was passed into the reaction solution and stirring was continued at 15 °C - 20 °C for 1 hour until the reaction solution became turbid. After completion of the reaction, the reaction mixture was washed with a mixed solvent of ethyl acetate/ethanol (4:1, v/v) and dried to afford (1S)-4,5-dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride (2.38 g, 95% yield).

References

[1] Patent: CN104557573, 2018, B. Location in patent: Paragraph 0109; 0116; 0121; 0122
[2] Patent: US2005/261376, 2005, A1. Location in patent: Page/Page column 3

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