Oxalyl chloride → Quinuclidin-4-ylcarbonyl chloride hydrochloride

HRID 1828623Notes

Reaction equation

HRID 1828623 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-d5f91adbdde64106a780d0003e51a219
Source dataset
uspto-grants-2006_06
Patent number
USRE039128E1

Reaction notes

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