Potassium Carbonate → HCID 19799596, compound

HRID 1032162Notes

Reaction equation

HRID 1032162 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.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>O1CCCC1.O.C(O)(C)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[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:21]2[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]2)=[O:11])[CH2:7]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 444972Fumaric AcidHCID 15042235HCID 15042235, compound

Product 1

HCID 19799596HCID 19799596, compoundYield 95.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.8 g (0.01 mole) of crude 3-(3,4-dichlorophenoxy)-1-azetidinecarbonyl chloride in 25 ml of tetrahydrofuran was treated with 1 g (0.01 mole) of 1-methylpiperazine then with 1.42 g (0.01 mole) of potassium carbonate. After stirring for 30 min, approximately 2 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and an oil separated. Upon standing, this oil solidified and was collected by filtration, yielding 3.3 g of crude product. The solid was dissolved in 20 ml of isopropanol and treated with 1.16 g of fumaric acid dissolved in 25 ml of boiling isopropanol. The volume was reduced to 30 ml by heating under a stream of nitrogen and upon cooling, the precipitated salt was collected by filtration, yielding 1.35 g (95.9%) of white crystals, m.p. 187°-188° C.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hr
  3. customan oil separated
  4. filtrationwas collected by filtration
  5. customyielding 3.3 g of crude product
  6. temperatureby heating under a stream of nitrogen
  7. temperatureupon cooling
  8. filtrationthe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-8e6f57f2ac804281bea05e52aab508de
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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