Potassium Carbonate → 3-(4-Fluorophenoxy)-N-(2-propynyl)-1-azetidinecarboxamide

HRID 974606Notes

Reaction equation

HRID 974606 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH2:25])[C:23]#[CH:24]>O1CCCC1.O>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:25][CH2:22][C:23]#[CH:24])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 239041PropargylamineHCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 150534403-(4-Fluorophenoxy)-N-(2-propynyl)-1-azetidinecarboxamideYield 174.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.52 g (0.022 mole) of crude 3-(4-fluorophenoxy)-1-azetidine carbonyl chloride and 3 g (0.02 mole) of potassium carbonate in 30 ml of tetrahydrofuran was cooled in an ice bath and while stirring treated with 1.1 g (0.02 mole) of propargylamine added dropwise. After stirring for 5 hr, the reaction mixture was diluted with 250 ml of water and the resulting solid collected by filtration to yield 8.67 g of wet product. Recrystallization from acetone after filtration to remove some amorphous material, gave a tacky solid. A second recrystallization from benzene after treating with charcoal yielded 2.7 g (50%) of beige crystals, m.p. 106°-108° C.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionadded dropwise
  3. stirringAfter stirring for 5 hr
  4. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-eb98af51b55a48c283d1271594879eaa
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

Loading…