Hydrochloric Acid → 7-Bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride

HRID 241087Notes

Reaction equation

HRID 241087 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][C:6]=2[CH:19]=1.C(O)C.[ClH:23].O1CCOCC1>C(OCC)C>[ClH:23].[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 25220760tert-Butyl 7-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 668201377-Bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-dimethylethyl 7-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (10 g, 30.5 mmol) was taken into hot ethanol (10 mL) followed by addition of 4 M hydrogen chloride in dioxane solution (2.1 eq, 16 mL) and the resulting solution was allowed to slowly cool to ambient temperature over one hour. An excess of ethyl ether was then added and the resulting slurry was filtered. The filter cake was washed with ethyl ether and dried to give 7-bromo-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride (7.9 g, 98% yield) as a colorless crystalline solid. MS (EI) for C9H10NOBr: 229 (MH+).

Workup

  1. filtrationthe resulting slurry was filtered
  2. washThe filter cake was washed with ethyl ether
  3. customdried

Sources & evidence

ORD record
ord-236090125a054c49b7aaa8c573f5deca
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

Loading…