Potassium Iodide → 1-[7-(Cyclopropylmethoxy)naphth-1-yl]piperazine

HRID 260670Notes

Reaction equation

HRID 260670 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[C:13]3[NH2:16])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Cl.Cl[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][CH:12]=[C:13]3[N:16]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium Carbonate2×HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 224002667-(Cyclopropylmethoxy)naphthalene-1-amine

Product 1

HCID 224002621-[7-(Cyclopropylmethoxy)naphth-1-yl]piperazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.7 g (0.036 mol) of 7-(cyclopropylmethoxy)naphthalene-1-amine, 6 g (0.036 mol) of bis(2-chloroethyl)amine hydrochloride, 50 ml of butanol and approximately 50 mg of potassium iodide is heated at reflux for 10 h under a nitrogen atmosphere. 2.5 g (0.018 mol) of potassium carbonate are added and heating at reflux is continued for 10 h, and then, twice, a further 1.25 g (0.009 mol) of potassium carbonate are added and the mixture is heated at reflux for 10 h. The butanol is evaporated. The residue is taken up in 100 ml of dichloromethane and 50 ml of 10% sodium hydroxide solution. The mixture is stirred in the presence of carbon black and filtered. The organic phase is separated and dried over magnesium sulphate. The solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, eluting with a 90:10 mixture of dichloromethane/methanol. After evaporation of the solvent, 4.2 g of an oily product are obtained which is used as it is in the following step.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 10 h under a nitrogen atmosphere
  3. temperatureheating
  4. temperatureat reflux
  5. temperaturethe mixture is heated
  6. temperatureat reflux for 10 h
  7. customThe butanol is evaporated
  8. filtrationfiltered
  9. customThe organic phase is separated
  10. dry with materialdried over magnesium sulphate
  11. customThe solvent is evaporated under reduced pressure
  12. customthe residue is purified by chromatography on a column of silica gel
  13. washeluting with a 90:10 mixture of dichloromethane/methanol
  14. customAfter evaporation of the solvent, 4.2 g of an oily product
  15. customare obtained which

Sources & evidence

ORD record
ord-8c5dc0aa631f48d8850537564ca1a45f
Source dataset
uspto-grants-1996_06
Patent number
US05530002

Reaction notes

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