Sodium Hydroxide → N-((1R)-1-Cyclohexylethyl)-4-phenyl-1-phthalazinamine

HRID 2211111Notes

Reaction equation

HRID 2211111 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[CH:18]1([C@H:24]([NH2:26])[CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Na+]>CN1CCCC1=O>[CH:18]1([C@H:24]([NH:26][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:4][N:3]=2)[CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2721091-Chloro-4-phenylphthalazineHCID 10997046(-)-1-Cyclohexylethylamine

Product 1

HCID 9840534N-((1R)-1-Cyclohexylethyl)-4-phenyl-1-phthalazinamineYield 75.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

722 mg (3.0 mmol) of 1-chloro-4-phenylphthalazine and 1.15 g (9.0 mmol) of (R)-(-)-1-cyclohexylethylamine were added to 2 ml of N-methylpyrrolidone, and the resultant mixture was stirred at 120° to 130° C. for 6 hours under heating. After the end of the reaction, the mixture was cooled. 20 ml of an aqueous 5% NaOH solution was added to the mixture and the solution was extracted with chloroform. The organic layer was dried over MgSO4, concentrated, purified by silica gel chromatography (eluent: ethyl acetate:hexane:chloroform=1:3:1) and recrystallized from ether-chloroform, thereby obtaining 751 mg of (R)-1-(1-cyclohexylethylamino)-4-phenylphthalazine.

Workup

  1. temperatureunder heating
  2. customAfter the end of the reaction
  3. temperaturethe mixture was cooled
  4. extractionthe solution was extracted with chloroform
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (eluent: ethyl acetate:hexane:chloroform=1:3:1)
  8. customrecrystallized from ether-chloroform

Sources & evidence

ORD record
ord-97297e895c5c42afa5b59a0b69bf0972
Source dataset
uspto-grants-1995_10
Patent number
US05462941

Reaction notes

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