Methyl quinuclidin-3-ylideneacetate hydrochloride → 2-(1-Azabicyclo(2.2.2)octan-3-ylidene)acetic acid hydrochloride

HRID 1923399Notes

Reaction equation

HRID 1923399 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>[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[CH:10][C:11]([OH:13])=[O:12])[CH2:3]2

Participants

3

Reactant 1

HCID 67401072Methyl quinuclidin-3-ylideneacetate hydrochloride

Product 1

HCID 674019582-(1-Azabicyclo(2.2.2)octan-3-ylidene)acetic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl quinuclidin-3-ylideneacetate hydrochloride (1 g) was heated in concentrated hydrochloric acid (10 ml) at 60° C. for 18 hrs and the solution evaporated to dryness. The residue was kept under vacuum over P2O5 for 3 days to give quinuclidin-3-ylidene acetic acid hydrochloride, 0.91 g (97%) as a white solid; 1H NMR (D2O) inter alia 5.77 (broad s) and 5.86 (broad s) (ca. 1:1, vinyl protons of the two geom. isomers).

Workup

  1. customthe solution evaporated to dryness

Sources & evidence

ORD record
ord-f8aea18b20ae4bfba7d3591f0e2727aa
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

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