Water → HCID 13534234, compound

HRID 464429Notes

Reaction equation

HRID 464429 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10](Cl)=[O:11])[CH2:6]1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][NH2:28].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([NH:28][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[O:11])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 202630113-(2,3-Dichlorophenoxy)-1-pyrrolidinecarbonyl Chloride

Product 1

HCID 13534234HCID 13534234, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution 11.8 g (0.04 mole) of 3-(2,3-dichlorophenoxy)-1-pyrrolidinecarbonyl chloride in 50 ml of chloroform was stirred at 5° C. in an ice bath while the following were added in order: 25 g of ice, 5.52 g of potassium carbonate and 3.87 g (0.044 mole) of N,N-dimethylethylenediamine. The resulting mixture was stirred for 20 hours and worked up by adding additional water followed by separation of the organic phase. The chloroform solution was dried over magnesium sulfate, filtered and concentrated in vacuo to a dark amber oil, 14 g, which solidified on standing. TLC analysis (10% methanol/chloroform) showed 3 spots; therefore, the crude product was chromatographed on 50 g of Fluorisil. Elution with chloroform gave a dark forerun which was discarded, the main portion was collected and rechromatographed through a 50 g Florisil column. The column was washed with 200 ml of methanol and the 2 fractions (chloroform and methanol) were combined before concentrating on a rotary evaporator to give a light amber oil which solidified. Recrystallization from isopropyl ether gave a beige crystalline product; 4.5 g (34%), m.p. 94°-95° C.

Workup

  1. additionwere added in order
  2. customfollowed by separation of the organic phase
  3. dry with materialThe chloroform solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a dark amber oil, 14 g, which
  6. customtherefore, the crude product was chromatographed on 50 g of Fluorisil
  7. washElution with chloroform
  8. customgave a dark forerun which
  9. customthe main portion was collected
  10. customrechromatographed through a 50 g Florisil column
  11. washThe column was washed with 200 ml of methanol
  12. concentrationbefore concentrating on a rotary evaporator
  13. customto give a light amber oil which
  14. customRecrystallization from isopropyl ether
  15. customgave a beige crystalline product

Sources & evidence

ORD record
ord-e66b923a75a043cfad254d5990fda233
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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