Potassium Carbonate → 1-(4-Chlorobenzoyl)-1-(4-methylpiperazin-1-yl)-cyclopropane

HRID 1649636Notes

Reaction equation

HRID 1649636 reaction equation
Br[CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7])[CH2:3][CH2:4]Cl.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>CN(C)C=O.CO>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:2]2([N:19]3[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]3)[CH2:4][CH2:3]2)=[O:7])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 531671-MethylpiperazineHCID 1071672-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-one

Product 1

HCID 137116841-(4-Chlorobenzoyl)-1-(4-methylpiperazin-1-yl)-cyclopropaneYield 50.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 29.6 g (0.1 mol) of 4-chlorophenyl 1-bromo-3-chloropropyl ketone in 30 ml of dimethylformamide is added dropwise to a mixture of 10.4 g of N-methyl piperazine and 14 g of potassium carbonate in 30 ml of dimethylformamide at room temperature. Stirring is continued for 3 hours, after which a solution of 9 g of potassium hydroxide in 30 ml of methanol is added dropwise. The reaction mixture is stirred for a further hour at 50° C. and evaporated down in vacuo. The residue is taken up in ethyl acetate/water, and the organic phase is separated off, washed with water, dried over sodium sulphate and evaporated down in vacuo. The residue is chromatographed over silica gel using chloroform/ethanol (97:3). 14 g (50.3% of theory) of 1-(4-chlorobenzoyl)-1-(4-methylpiperazin-1-yl)-cyclopropane are obtained as a reddish oil, which can be directly used further.

Workup

  1. stirringThe reaction mixture is stirred for a further hour at 50° C.
  2. customevaporated down in vacuo
  3. customthe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated down in vacuo
  7. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-e580e8e293d848279ef27c2fabc2d182
Source dataset
uspto-grants-1990_05
Patent number
US04921528

Reaction notes

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