Potassium Carbonate → HCID 15053401, compound

HRID 2081476Notes

Reaction equation

HRID 2081476 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][CH:6]1[CH2:9][N:8]([C:10]([N:26]2[CH2:27][CH2:28][N:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)[CH2:24][CH2:25]2)=[O:11])[CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 15042235HCID 15042235, compound

Product 1

HCID 15053401HCID 15053401, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.8 g (0.01 mole) of 3-(3,4-dichlorophenoxy)-1-azetidinecarbonyl chloride in 25 ml of tetrahydrofuran was treated in turn with 1.6 g (0.01 mole) of 1-(2-pyridyl)piperazine and 1.4 g (0.01 mole) of potassium carbonate. After 30 min, a solid had precipitated which dissolved when approximately 2 g of ice was added. After stirring for 18 hr, the reaction mixture was diluted with 200 ml of water and a paste-like solid separated which was filtered to yield 3.3 g of crude product. After several attempts to recrystallization from methyl isobutyl ketone, it was recrystallized from acetonitrile to yield 1.25 g (30.7%) of fine white crystals, m.p. 153.5°-154.5° C.

Workup

  1. customa solid had precipitated which
  2. dissolutiondissolved when approximately 2 g of ice
  3. additionwas added
  4. additionthe reaction mixture was diluted with 200 ml of water
  5. customa paste-like solid separated which
  6. filtrationwas filtered
  7. customto yield 3.3 g of crude product
  8. customAfter several attempts to recrystallization from methyl isobutyl ketone, it
  9. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-14bbaaf854be4b9489a51829558c3855
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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