Hydrochloric Acid → 8-Chloro-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine

HRID 220813Notes

Reaction equation

HRID 220813 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6](C(C3C=CC=CC=3)=O)[CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57555329(3-Chloro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-phenyl-methanone

Product 1

HCID 575553108-Chloro-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepineYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3-Chloro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-phenyl-methanone from Example E25.2 (783 mg, 2.7 mmol) was dissolved in dioxan (10 ml) and 6M HCl aqueous solution (50 ml) was added. The mixture was heated at reflux for 20 h then concentrated in vacuo and azeotroped with toluene. The residue was dissolved in diethyl ether and water, basified with NaHCO3 and the layers were partitioned. The organic layer was washed with brine, dried and concentrated in vacuo to yield the title compound (280 mg, 47%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 h
  3. concentrationthen concentrated in vacuo
  4. customazeotroped with toluene
  5. dissolutionThe residue was dissolved in diethyl ether
  6. customthe layers were partitioned
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e13aa5bebcd242078da81bccf431b438
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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