Potassium Carbonate → HCID 15053458, compound

HRID 1032155Notes

Reaction equation

HRID 1032155 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23]([NH2:26])[C:24]#[CH:25]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11]([NH:26][CH2:23][C:24]#[CH:25])=[O:12])[CH2:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 19799594HCID 19799594, compound

Product 1

HCID 15053458HCID 15053458, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.85 g (0.02 mole) of 3-(3-methoxyphenoxy)-1-azetidinecarbonyl chloride and 2.8 g (0.02 mole) of anhydrous potassium carbonate in 20 ml of tetrahydrofuran was stirred while 1.1 g (0.02 mole) of 2-propynylamine was added dropwise from a needle and syringe. After stirring for 30 min, a small piece of ice was added and stirring continued for 17 hr. The reaction mixture was diluted with 200 ml of water then extracted with 3×50 ml of methylene chloride. The combined extracts were dried by passing through Whatman phase separating paper then concentrated in vacuo to an oily residue (3.73 g). This residue was dissolved in 30 ml of methylene chloride and chromatographed in three portions (3 runs) on a spinning TLC plate (chromatotron) with an ethyl acetate-methylene chloride gradient from 10%-100% ethyl acetate. A white solid (1.8 g) was obtained on concentration of the product fractions. Recrystallization from isopropyl ether yielded 0.93 g (17.9%) of white crystalline product, m.p. 121°-123° C.

Workup

  1. additionwas added dropwise from a needle and syringe
  2. additiona small piece of ice was added
  3. stirringstirring
  4. waitcontinued for 17 hr
  5. extractionthen extracted with 3×50 ml of methylene chloride
  6. customThe combined extracts were dried
  7. customseparating paper
  8. concentrationthen concentrated in vacuo to an oily residue (3.73 g)
  9. dissolutionThis residue was dissolved in 30 ml of methylene chloride
  10. customchromatographed in three portions (3 runs) on a spinning TLC plate (chromatotron) with an ethyl acetate-methylene chloride gradient from 10%-100% ethyl acetate

Sources & evidence

ORD record
ord-6c1cbe9c9e7847698d8cbb52ed915b7b
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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