Hydrochloric Acid → 3-fluoro-6,10b-dihydro-1aH-dibenzo-[3,4:6,7]cyclohept[1,2-b]oxirene

HRID 47224Notes

Reaction equation

HRID 47224 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.Cl.Cl.CC([OH:22])C>C(OCC)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]3[O:22][CH:10]3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21912024Isopropanol hydrochlorideHCID 227441622-fluoro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 865887003-fluoro-6,10b-dihydro-1aH-dibenzo-[3,4:6,7]cyclohept[1,2-b]oxireneYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 1 was dissolved in diethyl ether (20 ml) and converted into the hydrochloric acid salt (1:1) by dropwise addition of 6 N HCl/2-propanol. The solvent was evaporated. The residue was triturated under boiling 2-propanone, filtered off and dried, yielding 2.17 g (43%) of (±)-(2α,3aβ,12bα)-11-fluoro-3,3a,8,12b-tetrahydro-N, N-dimethyl-2H-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan-2-methanamine hydrochloride (compound 2; mp. 239.1° C.).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was triturated under boiling 2-propanone
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-26278836630c419db0cc219d547fda6f
Source dataset
uspto-grants-2004_03
Patent number
US06699858B2

Reaction notes

Loading…