Cyclopropylamine → (E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamide

HRID 1954861Notes

Reaction equation

HRID 1954861 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>ClCCl>[CH:15]1([NH:18][C:12](=[O:13])/[CH:11]=[C:8]2\[CH2:7][CH2:6][C:5]3[C:9]\2=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 15491026(E)-2-(6-fluoro-1-indanylidene)acetyl chloride

Product 1

HCID 11746481(E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold stirred solution of (E)-2-(6-Fluoro-1-indanylidene)acetyl Chloride in dichloromethane (50 ml) was added cyclopropylamine (1.65 g, 28.86 mmol) and the reaction was warmed to room temperature overnight. The reaction was evaporated in vacuo to a solid residue. This residue was dissolved in ethyl acetate (300 ml) washed with water (75 ml), and the organic layer was concentrated by spin evaporation in vacuo. The residue was chromatographed on silica gel using ethyl acetate-hexanes (0:1 to 1:1 gradient) as eluent. Fractions containing only the product were combined and concentrated by spin evaporation in vacuo. Recrystallization of the residue from dichloromethane-hexanes gave 1.6 g (76%) of (E)-N-cyclopropyl-2-(6-fluoro-1-indanylidene)acetamide as a white powdery solid, m.p. 124-127° C.

Workup

  1. customThe reaction was evaporated in vacuo to a solid residue
  2. dissolutionThis residue was dissolved in ethyl acetate (300 ml)
  3. washwashed with water (75 ml)
  4. concentrationthe organic layer was concentrated by spin evaporation in vacuo
  5. customThe residue was chromatographed on silica gel
  6. additionFractions containing only the product
  7. concentrationconcentrated by spin evaporation in vacuo
  8. customRecrystallization of the residue from dichloromethane-hexanes

Sources & evidence

ORD record
ord-a13f7b8212c0448087f5f57d33a4ff68
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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