Methylamine → Ivabradine Impurity 1 Hydrochloride

HRID 648958Notes

Reaction equation

HRID 648958 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]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 13319974Ivabradine Impurity 1 Hydrochloride

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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.

Workup

  1. customThen, the cooled reaction product
  2. extractionextracted with methylene chloride
  3. customAfter the extract has been dried
  4. concentrationconcentrated
  5. customthe hydrochloride is precipitated from acetone/ether with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-d420edbe2c5f4f03bfb4175b4f2c0689
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

Loading…