Hydrochloric Acid → 2-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)ethanol dihydrochloride

HRID 862520Notes

Reaction equation

HRID 862520 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][CH2:11][CH:12]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[O:13]C2CCCCO2)[CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].[ClH:44]>CC(C)=O.C(OCC)C.C(Cl)(Cl)Cl.O>[ClH:44].[ClH:44].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][CH2:11][CH:12]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[OH:13])[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 536974332-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane

Product 1

HCID 675973272-[2-(4-Methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)ethanol dihydrochloride

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

In 30 ml of acetone was dissolved 3.3 g of 2-[2-(4-methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)ethane. To the solution were added 3.46 g of p-toluenesulfonic acid monohydrate and 7 ml of water at room temperature. The resulting mixture was stirred at the same temperature for 30 minutes and further at 40° C. for 1 hour. The reaction mixture was added to a mixture of 60 ml of chloroform and 60 ml of ice water. The mixture was adjusted to pH 11 with a 10% aqueous sodium hydroxide solution. The organic layer was separated. The aqueous layer was extracted with 20 ml of chloroform. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was dissolved in 40 ml of acetone. Hydrogen chloride gas was blown into the solution with ice cooling. The resulting solution was stirred at room temperature for 30 minutes. Thereto was added 40 ml of diethyl ether. The resulting mixture was stirred at the same temperature for 30 minutes. The resulting crystals were collected by filtration, washed with acetone, and dried to obtain 2.35 g of 2-[2-(4-methylpiperazin-1-yl)ethoxy]-1-(1-naphthyl)ethanol dihydrochloride (compound No. 259).

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with 20 ml of chloroform
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue thus obtained
  7. stirringThe resulting solution was stirred at room temperature for 30 minutes
  8. stirringThe resulting mixture was stirred at the same temperature for 30 minutes
  9. filtrationThe resulting crystals were collected by filtration
  10. washwashed with acetone
  11. customdried

Sources & evidence

ORD record
ord-886b90855b394d4091c81e3dd002b98d
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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