Potassium Carbonate → HCID 19799611, compound

HRID 1032179Notes

Reaction equation

HRID 1032179 reaction equation
[F:1][C:2]([F:18])([F:17])[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:19](=O)([O-])[O-].[K+].[K+].C[CH:26]=[CH:27][CH2:28][NH2:29]>O1CCCC1.O>[OH2:6].[CH3:19][N:29]([CH2:28][CH:27]=[CH2:26])[C:11]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)[CH2:8]1)=[O:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 304472-Buten-1-amineHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799611HCID 19799611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 20 ml of tetrahydrofuran was treated with 0.72 g (0.01 mole) of N-methylallylamine. After stirring for 15 minutes, a piece of ice was added and stirring continued for 15 hr. The reaction mixture was diluted with water and the oil which separated was extracted into methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo (3.7 g). The crude oil was chromatographed on a 75 g silica gel column by eluting with chloroform. After the first crude material was washed from the column the three product fractions were combined and concentrated in vacuo, to yield 3 g (97%) of water-like oil.

Workup

  1. additiona piece of ice was added
  2. stirringstirring
  3. waitcontinued for 15 hr
  4. customthe oil which separated
  5. extractionwas extracted into methylene chloride (2×50 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo (3.7 g)
  8. customThe crude oil was chromatographed on a 75 g silica gel column
  9. washby eluting with chloroform
  10. washAfter the first crude material was washed from the column the three product fractions
  11. concentrationconcentrated in vacuo
  12. customto yield 3 g (97%) of water-like oil

Sources & evidence

ORD record
ord-8ae342c5aaea472d824d813e3300de68
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

Loading…