1,3-Dichloroacetone → HCID 18700213, compound

HRID 2288602Notes

Reaction equation

HRID 2288602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][C:16]([CH2:18]Cl)=[O:17]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][C:16](=[O:17])[CH2:18][N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 752601-(4-Fluorophenyl)piperazine

Product 1

HCID 18700213HCID 18700213, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)piperazine (12 g) in acetone (40 ml) kept at reflux temperature a solution of 1,3-dichloroacetone (1.3 g) in acetone (10 ml) was added dropwise. The mixture was refluxed for another 2 hours. Acetone was evaporated in vacuo. The remaining viscous oil was subjected to column chromatography on silica gel (eluted with ethyl acetate/ethanol/triethylamine 80:20:4). The title compound 13a crystallized from diethyl ether. Yield 0.6 g. Mp 106-107° C. 1H NMR (CDCl3) δ 2.70 (t,8H), 3.15 (t,8H), 3.45 (s, 4H), 6.85-7.00 (m,8H).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for another 2 hours
  3. customAcetone was evaporated in vacuo
  4. customThe title compound 13a crystallized from diethyl ether

Sources & evidence

ORD record
ord-968d1e0955274b0f8c793f2da6d8d9ad
Source dataset
uspto-grants-2000_07
Patent number
US06090808

Reaction notes

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