Hydrochloric Acid → 7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

HRID 621432Notes

Reaction equation

HRID 621432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C:9](=O)[CH2:8][C:7]=2[CH:14]=1.B.[ClH:16]>O1CCCC1>[ClH:16].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 135206858-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 212429067-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 8-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine (20.4 g, 0.105 m) in tetrahydrofuran (500 ml) was added to 1 M borane in tetrahydrofuran (300 ml) stirred at 5°. The mixture was heated to reflux for 2 hours, cooled, treated with 3N hydrochloric acid (300 ml), concentrated in vacuo to remove tetrahydrofuran and heated to reflux for 1 hour. The mixture was concentrated in vacuo, filtered and the filter cake was dissolved in methanol, heated to reflux, dried with magnesium sulfate and concentrated in vacuo to afford 7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride, m.p. 229°-231°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto remove tetrahydrofuran
  6. temperatureheated
  7. temperatureto reflux for 1 hour
  8. concentrationThe mixture was concentrated in vacuo
  9. filtrationfiltered
  10. dissolutionthe filter cake was dissolved in methanol
  11. temperatureheated
  12. temperatureto reflux
  13. dry with materialdried with magnesium sulfate
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1675038d8f941d5ae3a67dbb80e24d3
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

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