Thionyl Chloride → 3-Quinuclidinecarbonyl chloride Hydrochloride

HRID 722169

Reaction equation

HRID 722169 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([OH:12])=O)[CH2:3]2.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[ClH:15].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([Cl:1])=[O:12])[CH2:3]2

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

Product 1

HCID 126734373-Quinuclidinecarbonyl chloride Hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

500 mg (2.61 mmol) of 3-quinuclidinecarboxylic acid hydrochloride (Orlek et al., J. Med. Chem. 1991, 34, 2726) are boiled together with 1.9 ml (26.09 mmol) of thionyl choride under reflux for 2 h. The reaction mixture is freed of thionyl chloride under reduced pressure. 20 ml portions of toluene are twice added and evaporated to dryness. The product obtained in this way is reacted further without further purification.

Workup

  1. temperatureunder reflux for 2 h
  2. customevaporated to dryness
  3. customThe product obtained in this way
  4. customis reacted further without further purification

Sources & evidence

ORD record
ord-da64b4506e7f45239d54214f6ee18580
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Linked notes

Loading…