| Identification | More | [Name]
(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride | [CAS]
866783-13-3 | [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 | [EINECS(EC#)]
617-905-7 | [Molecular Formula]
C12H18ClNO2 | [MDL Number]
29214990 | [Molecular Weight]
243.73 | [MOL File]
866783-13-3.mol |
| Chemical Properties | Back Directory | [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) |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [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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