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

HRID 862763Notes

Reaction equation

HRID 862763 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.; NMR (DMSO-d6): d 8.03 (d, 1H, J=3.9 Hz, NH), 7.45-7.38 (m, 1H, Ar), 7.28-7.14 (m,2H, Ar), 6.30 (s, 1H, =CH, 3.23-3.21 (m, 2H, CH2), 2.99-2.96 (m, 2H, CH2), 2.72 (m, 1H, NCH), 0.71-0.39 (2ms, 4H, CH2 -CH2); steady state nOe: irradiation at d6.30, observed 15% nOe at d 8.03 and 20% nOe at d 7.23.

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-fc14fe31f59044198188b231d7f2d735
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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