Hydrochloric Acid → 6-(3-Pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene dihydrochloride

HRID 597975Notes

Reaction equation

HRID 597975 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]3[CH2:14][CH:12]([CH:13]=2)[CH2:11][NH:10][CH2:9]3)[CH:2]=1.[ClH:15].C(OCC)C>C(O)C.C(O)(C)C>[ClH:15].[ClH:15].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]3[CH2:14][CH:12]([CH:13]=2)[CH2:11][NH:10][CH2:9]3)[CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 574855266-(3-Pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene

Product 1

HCID 574857746-(3-Pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene dihydrochlorideYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

6-(3-Pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene (190 mg, 1.0 mmol) was dissolved in ethanol (5 ml), and 12 N HCl (2 ml) was added. The solution was sonicated for 3 min, and then concentrated by azeotropic rotary evaporation with ethanol (3×5 ml) to yield a fluffy solid. Then the salt was dissolved in hot isopropanol (2 ml), and diethyl ether was added until a milky solution formed. Cooling in the freezer produced a light brown solid. The solid was filtered, washed with diethyl ether, and dried under high vacuum to yield 6-(3-pyridinyl)-3-azabicyclo[3.2.1]oct-6-ene dihydrochloride, (230 mg, 87%, m.p. 192-195° C.).

Workup

  1. customThe solution was sonicated for 3 min
  2. concentrationconcentrated by azeotropic rotary evaporation with ethanol (3×5 ml)
  3. customto yield a fluffy solid
  4. customformed
  5. temperatureCooling in the freezer
  6. customproduced a light brown solid
  7. filtrationThe solid was filtered
  8. washwashed with diethyl ether
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-81b02cc761a943eba28f0c0dead93723
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

Loading…