Potassium Iodide → HCID 57440110, compound

HRID 1860381Notes

Reaction equation

HRID 1860381 reaction equation
ClC1C=CC(N)=CC=1.[I-].[K+].[CH2:11]([O:13][C:14]([C@H:16]1[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:17]1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)=[O:15])[CH3:12]>Cl>[CH2:24]([O:23][C:21]([CH:18]1[CH2:19][CH2:20][CH:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[N:17]1[C:26]1[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 78124-ChloroanilineHCID 86585101HCID 86585101, compound

Product 1

HCID 57440110HCID 57440110, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl meso-2,5-dibromo adipate (5.0 g, 13.89 mmol), 4-chloro-aniline (6.2 g, 48.60 mmol), potassium iodide (0.032 g, 0.193 mmol) were combined and heated at 80° C. for 3 h then 90° C. for ½ h. Mix was cooled, diluted with 6N hydrochloric acid (400 mL) and extracted with ethyl acetate (3×400 mL). The combined organic layers were washed with water (5×200 mL), brine (200 mL), dried with magnesium sulfate and concentrated to yield a mixture of cis and trans 1-(4-Chloro-phenyl)-pyrrolidine-2,5-dicarboxylic acid diethyl ester (4.53 g, 100%) as a brown oil. Oil was used without further purification.

Workup

  1. additionMix
  2. temperaturewas cooled
  3. extractionextracted with ethyl acetate (3×400 mL)
  4. washThe combined organic layers were washed with water (5×200 mL), brine (200 mL)
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customto yield
  8. customOil was used without further purification

Sources & evidence

ORD record
ord-be9f0758d9334149b6c35dd42706a03a
Source dataset
uspto-grants-2003_03
Patent number
US06531468B2

Reaction notes

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