HCID 13556875, compound → 8-Chloro-4,5-dihydro-1-phenyl-3H-2-benzazepine hydrochloride

HRID 464931Notes

Reaction equation

HRID 464931 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15](=O)[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3C2=O)=[C:4](C(=O)C2C=CC=CC=2)[CH:3]=1>C(O)C.[OH-].[Na+].Cl.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:8][CH2:9][CH2:10][N:11]=[C:15]([C:14]3[CH:13]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[CH:7]=1

Participants

6

Reactant 1

HCID 13556875HCID 13556875, compound

Product 1

HCID 135568788-Chloro-4,5-dihydro-1-phenyl-3H-2-benzazepine hydrochloride

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5.1 g (12.6 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropane in 100 ml of ethanol and 20 ml of 3N sodium hydroxide was refluxed for 2 hr. The solution was diluted with 60 ml of 3N hydrochloric acid and refluxed for 12 hr. The mixture was diluted with water and extracted with ether. The aqueous layer was separated, made alkaline with dilute sodium hydroxide, and extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was purified by plug filtration (silica gel, 10 g; eluent, methylene chloride) and the eluent was acidified with methanolic hydrogen chloride. The solution was concentrated at reduced pressure to dryness and the residue was crystallized from a mixture of isopropanol and ether to give a colorless solid, mp 234°-235° C. Recrystallization from a mixture of methylene chloride and ether gave colorless needles, mp 234°-235° C. dec.

Workup

  1. temperaturerefluxed for 12 hr
  2. extractionextracted with ether
  3. customThe aqueous layer was separated
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure to dryness
  8. filtrationThe residue was purified by plug filtration (silica gel, 10 g; eluent, methylene chloride)
  9. concentrationThe solution was concentrated at reduced pressure to dryness
  10. customthe residue was crystallized from a mixture of isopropanol and ether
  11. customto give a colorless solid, mp 234°-235° C
  12. customRecrystallization
  13. additionfrom a mixture of methylene chloride and ether
  14. customgave colorless needles, mp 234°-235° C. dec.

Sources & evidence

ORD record
ord-fa7777c9d5a244d3933badd18e903767
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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