Hydrochloric Acid → 2-(Quinuclidin-3-yl)acetic acid hydrochloride

HRID 1828626Notes

Reaction equation

HRID 1828626 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[CH:10][C:11]([O:13]C)=[O:12])[CH2:3]2.Cl>[Pd].C(O)C>[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([OH:13])=[O:12])[CH2:3]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67401072Methyl quinuclidin-3-ylideneacetate hydrochloride

Product 1

HCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochlorideYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl quinuclidin-3-ylideneacetate hydrochloride (Example 18, Step 1) (2 g), ethanol (50 ml), 2M hydrochloric acid (5 ml) and 10% Pd/C (1 g) was stirred for 24 hours under H2 at atmospheric pressure, filtered through celite and evaporated to dryness. The residue was dissolved in concentrated hydrochloric acid (10 ml). heated at 60° C. for 18 hours, treated with a further 10 ml of concentrated hydrochloric acid, heated at 80° C. for 6 hours and evaporated to dryness. The residue was kept under vacuum over P2O5 for 3 days to give the title compound as a white solid (1.8 g); MS (+ve ion electrospray) m/z 170 (MH+, 100%).

Workup

  1. filtrationfiltered through celite
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in concentrated hydrochloric acid (10 ml)
  4. additiontreated with a further 10 ml of concentrated hydrochloric acid
  5. temperatureheated at 80° C. for 6 hours
  6. customevaporated to dryness
  7. waitThe residue was kept under vacuum over P2O5 for 3 days

Sources & evidence

ORD record
ord-b0ef6f6966df4f418b4664af4187724c
Source dataset
uspto-grants-2006_06
Patent number
USRE039128E1

Reaction notes

Loading…