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| | (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Basic information | | Uses |
| Product Name: | (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride | | Synonyms: | (1S)-4,5-Dimethoxy-1-(Methylaminomethyl)-Benzocyclobutane Hcl;(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride;(7S)-3,4-Dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-methanamine hydrochloride;(1S)-4,5-Dimethoxy-1-(methylaminoethyl)benzocyclobutane HCl;(S)-N-[(4,5-diMethoxybenzocyclobut-1-yl)Methyl ]-N-MethylaMine h;(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)MethanaMine;3,4-diMethoxy-N-Methyl-bicyclo[4.2.0]octa-1,3,5-triene-7-MethanaMine hydrochloride;Bicyclo[4.2.0]octa-1,3,5-triene-7-MethanaMine, 3,4-diMethoxy-N-Methyl-, hydrochloride | | CAS: | 866783-13-3 | | MF: | C12H18ClNO2 | | MW: | 243.73 | | EINECS: | 617-905-7 | | Product Categories: | | | Mol File: | 866783-13-3.mol | ![(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Structure](CAS/GIF/866783-13-3.gif) |
| | (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 | | Major Application | pharmaceutical small molecule | | 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) |
| WGK Germany | WGK 3 | | HS Code | 29214990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Skin Irrit. 2 |
| | (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 |
| | (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride Preparation Products And Raw materials |
| Raw materials | Bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid, 3,4-dimethoxy-, (7R)--->(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid N-methyl-amide-->4,5-Dimethoxy-1-cyanobenzocyclobutane-->3-(2-BROMO-4,5-DIMETHOXYPHENYL)PROPANENITRILE-->(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine-->(3,4-DiMethyoxy-bicyclo(4,2,0)octa-1(6),2,4-trien-7-ylMethyl)-carbaMic acid ethyl ester-->Ivabradine Impurity 68-->4,5-Dimethoxybenzocyclobutene-1-carboxylic acid-->Acetic acid-->Ethanol |
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