Hydrochloric Acid → HCID 69196263, compound

HRID 2220201Notes

Reaction equation

HRID 2220201 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7](O)[C:8]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:4]=2[CH:3]=1.Cl>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[CH:6]=[CH:7][C:8]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 597724718-Bromo-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocine-12-ol

Product 1

HCID 69196263HCID 69196263, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 8-Bromo-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocine-12-ol (0.85 g, 2.5 mmole) in dioxane (10 mL) was added concentrated HCl (1 mL). The reaction was heated to reflux for 24 hours. The reaction mixture was concentrated and the residue obtained was dissolved in ethyl acetate, washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated to give 8-Bromo-2-chloro-5,6-dihydro-dibenzo[b,f]azocine (0.7 g, 87%). HPLC Rt=4.33 min. m/z=320 (M+H+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue obtained
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f82d12ae0da44a878ccd18ad06b932c9
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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