Hydrochloric Acid → 7,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3-dihydro-2H-3-benzazepin-2-one

HRID 420862Notes

Reaction equation

HRID 420862 reaction equation
[CH3:1][O:2][C:3]1[C:26]([O:27][CH3:28])=[CH:25][C:6]2[CH2:7][C:8](=[O:24])[N:9]([CH2:12][CH2:13][CH2:14][N:15](C)[C:16](=O)OC(C)(C)C)[CH:10]=[CH:11][C:5]=2[CH:4]=1.Cl.[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[C:26]([O:27][CH3:28])=[CH:25][C:6]2[CH2:7][C:8](=[O:24])[N:9]([CH2:12][CH2:13][CH2:14][NH:15][CH3:16])[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86643007tert-Butyl [3-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-3-benzazepin-3-yl)propyl]-methylcarbamate

Product 1

HCID 666577367,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3-dihydro-2H-3-benzazepin-2-oneYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 1.9 g (4.86 mmol) of the product obtained in Step 1 in 30 ml of ethanol and add to that solution 7 ml (24.3 mmol, 5 equivalents) of HCl in ethanol (3.5N). Heat overnight at 60° C. and evaporate the reaction mixture to dryness. The residue obtained is taken up in water, and the aqueous phase is then adjusted to pH=8 by adding 20% sodium hydroxide solution and extracted with dichloromethane. The organic phase is washed with water, dried over MgSO4, filtered and then evaporated to dryness. 1.1 g of the title product are obtained in the form of a colourless oil.

Workup

  1. customevaporate the reaction mixture to dryness
  2. customThe residue obtained
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-973b29c9959544f4913942605c9970ce
Source dataset
uspto-grants-2012_01
Patent number
US08097720B2

Reaction notes

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