Sulfuric Acid → HCID 49780356, compound

HRID 1914533Notes

Reaction equation

HRID 1914533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13]O.OS(O)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]2[CH2:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][CH2:5][C:4]=2[CH:15]=[CH:16][CH:17]=1.[Br:1][C:2]1[CH:17]=[CH:16][C:15]2[CH2:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 43229644HCID 43229644, compound

Product 2

HCID 49780356HCID 49780356, compoundHCID 49780357HCID 49780357, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(3-bromo-benzylamino)-phenyl]-methanol (0.180 mol) in DCM (50 mL) was added over a 5 hr period to a cooled (±−10 to −20° C.) solution of concentrated H2SO4 (500 mL). The ice-bath was then removed, and the mixture was stirred for one hour at rt. The reaction mixture was added to ice-water, cooled on ice, and alkalized with a 50% aqueous NaOH solution. The resulting mixture (±3 L) was extracted with DCM. The organic layer was separated, dried on MgSO4, filtered and the filtrate was concentrated in vacuo. A part (8 g) of this residue was purified via Supercritical Fluid Chromatography (SFC, column: Diacel AD-H 30×250 mm, mobile phase: 55% MeOH/45% CO2+0.2% isopropylamine, 40° C., 100 bar) to give 2 g of 10-bromo-6,11-dihydro-5H-dibenzo[b,e]azepine and 4.65 g of 8-bromo-6,11-dihydro-5H-dibenzo[b,e]azepine.

Workup

  1. customThe ice-bath was then removed
  2. additionThe reaction mixture was added to ice-water
  3. temperaturecooled on ice
  4. extractionThe resulting mixture (±3 L) was extracted with DCM
  5. customThe organic layer was separated
  6. customdried on MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customA part (8 g) of this residue was purified via Supercritical Fluid Chromatography (SFC, column: Diacel AD-H 30×250 mm, mobile phase: 55% MeOH/45% CO2+0.2% isopropylamine, 40° C., 100 bar)

Sources & evidence

ORD record
ord-920310f2031f4c4ea1b8a17cb2598ed8
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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