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

HRID 1716220Notes

Reaction equation

HRID 1716220 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C:4](=O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.O.NN.[OH-].[K+].Cl>C(O)COCCO>[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-one

Product 1

HCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineYield 47.8%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-benzo[b]azepin-5-one (5) (1.58 g, 9.80 mmol), hydrazine monohydrate (1.92 mL, 40.0 mmol), and KOH (3.3 g, 58.8 mmol) in diethylene glycol (50 mL) was heated to reflux for 6 hr under a N2 atmosphere. After cooling, the reaction was poured onto ice-cold water, neutralized with 1N HCl, and extracted with EtOAc. All the organics were washed with water and saturated NaCl. Dried over MgSO4, filtered, and concentrated to yield compound 6 (0.69 g). This crude material was used in the next step with out further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr under a N2 atmosphere
  3. temperatureAfter cooling
  4. additionthe reaction was poured onto ice-cold water
  5. extractionextracted with EtOAc
  6. washAll the organics were washed with water and saturated NaCl
  7. dry with materialDried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cbe235a082254bfc95ae8bea7d9a101a
Source dataset
uspto-grants-2010_09
Patent number
US07803790B2

Reaction notes

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