Oxalyl chloride → Quinuclidin-4-ylcarbonyl chloride hydrochloride

HRID 1923397Notes

Reaction equation

HRID 1923397 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][C:5]([C:10](O)=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[ClH:16].[N:2]12[CH2:9][CH2:8][C:5]([C:10]([Cl:1])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 667378251-Azabicyclo(2.2.2)octane-4-carboxylic acid hydrochloride

Product 1

HCID 13760941Quinuclidin-4-ylcarbonyl chloride hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Quinuclidine-4-carboxylic acid hydrochloride (0.192 g, 0.001 mole) was suspended in dichloromethane (5 ml) and dimethylformamide (1 drop) and oxalyl chloride (0.436 ml. 0.635 g, 0.005 mole) were added. The resulting suspension was heated to reflux under an atmosphere of argon for six hours. Following concentration of the suspension in vacuo the residue was suspended in dichloromethane, concentrated in vacuo and finally dried in vacuo to give the title compound as a pale brown solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux under an atmosphere of argon for six hours
  3. concentrationconcentrated in vacuo
  4. customfinally dried in vacuo

Sources & evidence

ORD record
ord-f8c36db196cd4f3cbec6c561bc16468e
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

Loading…