Ethyl 2-oxocyclohexylacetate → HCID 23043062, compound

HRID 2165568Notes

Reaction equation

HRID 2165568 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.[CH3:19][CH2:20][O:21][C:22]([CH2:24][CH:25]1[C:30](=O)[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:23]>>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:26]3[CH:25]([CH2:24][C:22]([O:21][CH2:20][CH3:19])=[O:23])[CH2:30][CH2:29][CH2:28][C:27]=3[C:15]3[C:10]2=[CH:11][CH:12]=[C:13]([F:16])[CH:14]=3)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 145912421-(p-Chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride

Product 1

HCID 23043062HCID 23043062, compoundYield 57.8%

Procedure

To 3.50 g of 1-(4-chlorobenzyl)-1-(4-fluorophenyl)hydrazine hydrochloride in 70 cc of iso-propan. (was added 2.23 g of ethyl 2-cyclohexanone acetate. The reaction was refluxed under nitrogen for 16 hours. The resulting reaction mixture was then evaporated to dryness and the residue suspended in ether. The solid material was then filtered. The ether filtrate was washed with water, dried and evaporated. The resulting syrup was chromatographed on silica gel to give 2.8 g (42%) of the title compound.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 16 hours
  2. customThe resulting reaction mixture
  3. customwas then evaporated to dryness
  4. filtrationThe solid material was then filtered
  5. washThe ether filtrate was washed with water
  6. customdried
  7. customevaporated
  8. customThe resulting syrup was chromatographed on silica gel

Sources & evidence

ORD record
ord-6b0d501ae8744552bfe4c73711788d13
Source dataset
uspto-grants-1990_07
Patent number
US04940719

Reaction notes

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