Potassium Carbonate → HCID 15053456, compound

HRID 974623Notes

Reaction equation

HRID 974623 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10](Cl)=[O:11])[CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH2:25])[C:23]#[CH:24]>O1CCCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([NH:25][CH2:22][C:23]#[CH:24])=[O:11])[CH2:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 19799586HCID 19799586, compound

Product 1

HCID 15053456HCID 15053456, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 3.92 g (0.01 mole) of crude (57.59%) 3-(3-methylphenoxy)-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 15 ml of tetrahydrofuran was treated with 0.55 g (0.01 mole) of 2-propynylamine added dropwise from a needle and syringe. After 10 min, approximately 1 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated slowly solidified. The precipitated solid was collected by filtration to yield 4.7 g of crude wet product. After air drying, the solid was recrystallized from benzene-ligroin to yield 1.78 g (72.9%) of fine white crystals, m.p. 140°-142° C.

Workup

  1. additionadded dropwise from a needle and syringe
  2. waitcontinued for 18 hr
  3. customthe oil which separated slowly
  4. filtrationThe precipitated solid was collected by filtration
  5. customto yield 4.7 g of crude wet product
  6. customAfter air drying
  7. customthe solid was recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-68232b7a46364a53991cb5f52273cf61
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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