Hydrochloric Acid → 7,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)

HRID 657554

Reaction equation

HRID 657554 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=O)[NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.B.C1COCC1.C(O)C.[ClH:26]>C1COCC1>[ClH:26].[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2723981Borane;tetrahydrofuranHCID 114017697,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

Product 1

HCID 220040987,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

22.13 g (100 mmol) of the product obtained in Step 1, suspended in 250 mL of THF, are cooled to 0° C. There are then added, dropwise, over 15 minutes, 250 mL of borane/THF (1M in the THF) and heating is carried out at 80° C. for 24 hours. Cooling is carried out and there are then added, dropwise, 250 mL of ethanol, and then 2.6N ethanolic HCl. Heating at reflux is carried out for 40 minutes; some light insoluble material is filtered off and evaporation to dryness is carried out. The residue thereby obtained is recrystallised from a mixture of 150 mL of isopropanol and 20 mL of water to yield the desired product.

Workup

  1. additionThere are then added
  2. waitis carried out at 80° C. for 24 hours
  3. temperatureCooling
  4. additionthere are then added
  5. temperatureHeating
  6. temperatureat reflux
  7. waitis carried out for 40 minutes
  8. filtrationsome light insoluble material is filtered off
  9. customevaporation to dryness
  10. customThe residue thereby obtained
  11. customis recrystallised from a mixture of 150 mL of isopropanol and 20 mL of water

Sources & evidence

ORD record
ord-36f8f94c5ab04e7ea8422c96ea1e1876
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Linked notes

Loading…