Methylamine → Ivabradine Impurity 1 Hydrochloride
Reaction equation
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH3:21][NH2:22]>[OH-].[Na+]>[ClH:15].[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][NH:22][CH3:21])[CH2:10][CH2:11][C:5]=2[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
First, 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane (5.9 g, 0.020 mol) and methylamine (14 g, 0.45 mol) are heated to 130° C. for 1 hour in a sealed tube. Then, the cooled reaction product is taken up in semi-concentrated sodium hydroxide solution and extracted with methylene chloride. After the extract has been dried and concentrated, the hydrochloride is precipitated from acetone/ether with ethereal hydrochloric acid.