(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamine → Ivabradine

HRID 1894923Notes

Reaction equation

HRID 1894923 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH3:15])[CH2:6]2.[CH3:16][O:17][C:18]1[C:33]([O:34][CH3:35])=[CH:32][C:21]2[CH2:22][C:23](=[O:31])[N:24]([CH2:27][CH2:28][CH:29]=O)[CH2:25][CH2:26][C:20]=2[CH:19]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH3:15])[CH2:29][CH2:28][CH2:27][N:24]1[C:23](=[O:31])[CH2:22][C:21]3[CH:32]=[C:33]([O:34][CH3:35])[C:18]([O:17][CH3:16])=[CH:19][C:20]=3[CH2:26][CH2:25]1)[CH2:6]2

Participants

3

Reactant 2

HCID 11499437(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamineHCID 201441843-(7,8-Dimethoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propionaldehyde

Product 1

HCID 132999Ivabradine

Conditions

Temperature
85 °C

Procedure

1 mmol of [(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine and 1 mmol of 3-(7,8-dimethoxy-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)propanal are introduced into a clean and dry stainless-steel autoclave under an argon atmosphere. The mixture is degassed by three vacuum/argon cycles and 3 mL of distilled and degassed ethanol are added. The solution is stirred at 85° C. for one hour. The iron complex (5 mol %) is added under argon. The autoclave is then placed under hydrogen pressure (5 bars) and the reaction mixture is stirred at 85° C. for 16 hours and then the autoclave is returned to ambient temperature and decompressed.

Workup

  1. dry with materialdry stainless-steel autoclave under an argon atmosphere
  2. customThe mixture is degassed by three vacuum/argon cycles and 3 mL
  3. distillationof distilled
  4. customdegassed ethanol
  5. additionare added
  6. additionThe iron complex (5 mol %) is added under argon
  7. stirringthe reaction mixture is stirred at 85° C. for 16 hours
  8. customis returned to ambient temperature

Sources & evidence

ORD record
ord-b3d3321b184e400882c5d3eae47eac2c
Source dataset
uspto-grants-2013_08
Patent number
US08513410B2

Reaction notes

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