HCID 69746174, compound → HCID 69745305, compound

HRID 1815871Notes

Reaction equation

HRID 1815871 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[C:22]3[O:21][CH:20]=[C:19]([Cl:23])[C:18]=3[CH:17]=[C:16]([Cl:24])[C:15]=2[F:25])[C@H:10]([CH3:26])[CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:23].[CH3:26][C@H:10]1[C@@H:11]([C:14]2[C:22]3[O:21][CH:20]=[C:19]([Cl:23])[C:18]=3[CH:17]=[C:16]([Cl:24])[C:15]=2[F:25])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 69746174HCID 69746174, compound

Product 1

HCID 69745305HCID 69745305, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Fractions containing cis-1-(tert-butoxycarbonyl)-3-methyl-4-(3,5-dichloro-6-fluorobenzofur-7-yl)piperidine were combined and concentrated under reduced pressure to provide 0.107 gm. (Ion Spray MS: m/e=403 (M+1)). A solution of this material in 3.5 mL 4N hydrogen chloride in dioxane was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol. This solution was subjected to ion exchange chromatography (Varian SCX) and the column was eluted sequentially with methanol followed by 2N ammonia in methanol. Fractions containing cis-3-methyl-4-(3,5-dichloro-6-fluorobenzofur-7-yl)piperidine were combined and concentrated under reduced pressure. This residue was dissolved in diethyl ether and treated with hydrogen chloride in diethyl ether. The suspension was concentrated under reduced pressure and the residue suspended in diethyl ether. This suspension was filtered and to provide 0.066 gm of cis-3-methyl-4-(3,5-dichloro-6-fluorobenzofur-7-yl)piperidine hydrochloride as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto provide 0.107 gm
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol
  5. washthe column was eluted sequentially with methanol
  6. additionFractions containing cis-3-methyl-4-(3,5-dichloro-6-fluorobenzofur-7-yl)piperidine
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThis residue was dissolved in diethyl ether
  9. additiontreated with hydrogen chloride in diethyl ether
  10. concentrationThe suspension was concentrated under reduced pressure
  11. filtrationThis suspension was filtered

Sources & evidence

ORD record
ord-866f5e6c0043444983a71582e6c2e4a5
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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