Cyclopropylamine → HCID 13579376, compound

HRID 1589081Notes

Reaction equation

HRID 1589081 reaction equation
[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[C:9]([NH2:23])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:24]1(N)[CH2:26][CH2:25]1>C(O)C>[C:1]1([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=3)=[C:9]([NH:23][CH:24]3[CH2:26][CH2:25]3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 69828Cyclopropylamine2×HCID 13579285HCID 13579285, compound

Product 1

HCID 13579376HCID 13579376, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In this example, a mixture containing 5.0 g (0.0157 g mole) of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran and 8.96 g of cyclopropylamine in 50 ml of ethanol containing 5% water was refluxed for six days. At the end of this time, a sample of the reaction mixture was checked by thin layer chromatography and then an additional 8.96 g of cyclopropylamine was added. The mixture was refluxed for an additional 24 hours and then allowed to stand at room temperature over night. The mixture was then concentrated by evaporation under vacuum, affording a crude product oil. The crude product was chromatographed over silica gel eluting with 80:20 (V/V) petroleum ether and ethyl acetate. The product fractions were combined and evaporated in vacuo affording 2.07 g of the title compound Elemental Analysis Carbon calc.: 66.8%, found 67.4%; hydrogen calc.: 4.5%, found 4.7%; nitrogen calc.: 3.9%, found 4.6%; melting point 160°-164° C.

Workup

  1. temperaturewas refluxed for six days
  2. temperatureThe mixture was refluxed for an additional 24 hours
  3. waitto stand at room temperature over night
  4. concentrationThe mixture was then concentrated by evaporation under vacuum
  5. customaffording a crude product oil
  6. customThe crude product was chromatographed over silica gel eluting with 80:20 (V/V) petroleum ether and ethyl acetate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-36a69d75279c47b39577b0c812143b03
Source dataset
uspto-grants-1986_02
Patent number
US04568378

Reaction notes

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