Allylamine → Cis-2-Methyl-N-(2-propenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 974648Notes

Reaction equation

HRID 974648 reaction equation
[CH3:1][CH:2]1[CH:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][N:3]1[C:17](Cl)=[O:18].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([NH2:29])[CH:27]=[CH2:28]>O1CCCC1.O>[CH3:1][C@H:2]1[C@@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][N:3]1[C:17]([NH:29][CH2:26][CH:27]=[CH2:28])=[O:18]

Participants

6

Reactant 3

HCID 7853AllylamineHCID 11430Potassium CarbonateHCID 197996032-Methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride

Product 1

HCID 67885530Cis-2-Methyl-N-(2-propenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 67.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 4.02 g (0.01 mole) of crude (73%) 2-methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride cis isomer and 1.4 g (0.01 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 0.57 g (0.01 mole) of 2-propenylamine. After stirring for 15 minutes, a small piece of ice was added and stirring continued for 3 hr. The reaction mixture was diluted with water and the oil which separated was extracted with methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo (5.2 g). The crude produce was chromatographed on a 125 g silica gel column. Elution with chloroform washed impurities from the column and the produce was removed by eluting with an ethyl acetate/chloroform gradient (1-20%). The combined product fractions gave a pale yellow oil which solodified on standing and was recrystallized from isopropyl ether/hexane to give an oil which slowly crystallized, yielding 2.1 g (67.8%) of white product, m.p. 74°-77° C.

Workup

  1. additiona small piece of ice was added
  2. stirringstirring
  3. waitcontinued for 3 hr
  4. customthe oil which separated
  5. extractionwas extracted with methylene chloride (2×50 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo (5.2 g)
  8. customThe crude produce
  9. customwas chromatographed on a 125 g silica gel column
  10. washElution with chloroform washed impurities from the column
  11. customthe produce was removed
  12. washby eluting with an ethyl acetate/chloroform gradient (1-20%)
  13. customThe combined product fractions gave a pale yellow oil which
  14. customwas recrystallized from isopropyl ether/hexane
  15. customto give an oil which
  16. customslowly crystallized

Sources & evidence

ORD record
ord-a4ce110bbdca401284b7f729604523ae
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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