Potassium Carbonate → 1-Cyclopropyl-4-[(2-nitrophenyl)thio]piperazine

HRID 1382207Notes

Reaction equation

HRID 1382207 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][N:11]([CH2:25][CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O)([O-:3])=[O:2].[CH:38]1([NH2:41])[CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH:38]1([N:41]2[CH2:13][CH2:12][N:11]([S:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:25][CH2:26]2)[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 13850776HCID 13850776, compound

Product 1

HCID 138507771-Cyclopropyl-4-[(2-nitrophenyl)thio]piperazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 112 g (0.198 mol) of N-(2-nitrophenylsulphenyl)-bis[2-(4-toluenesulphonyloxy)-ethyl]amine, 16.7 g (0.29 mol) of cyclopropylamine and 82 g (0.6 mol) of powdered potassium carbonate in 3.3 l of isopropanol is heated under reflux for 6 hours. Thereafter, the mixture is concentrated in vacuo, the residue is taken up in 550 ml of methylene chloride and the mixture is washed with water, dried with sodium sulphate and concentrated. For purification, the crude product is filtered over 600 g of silica gel with methylene chloride as the mobile phase and the eluate is concentrated. Yield: 47 g of melting point 100°-102°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. concentrationThereafter, the mixture is concentrated in vacuo
  4. washthe mixture is washed with water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customFor purification
  8. filtrationthe crude product is filtered over 600 g of silica gel with methylene chloride as the mobile phase
  9. concentrationthe eluate is concentrated

Sources & evidence

ORD record
ord-d248b5b6be1445ce8b3b44e16f72e4ca
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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