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

HRID 263398Notes

Reaction equation

HRID 263398 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

To 400 ml of N-methylpyrrolidone, 144.4 g (0.6 mol) of 1-chloro-4-phenylphthalazine and 230 g (1.8 mol) of (R)-(-)-1-cyclohexylethylamine were added, and the mixture was heated to 120° to 130° C. for 6 hours with stirring. After completion of the reaction, the mixture was cooled and added with 4.0 l of 5% aqueous NaOH solution, and then extracted with chloroform. The organic layer was dried over MgSO4, concentrated and purified by silica gel column chromatography (eluent; ethyl acetate/hexane/chloroform=1:3:1). After recrystallization from ether/chloroform, 150.2 g of (R)-1-(1-cyclohexylethylamino)-4-phenylphthalazine was obtained. m.p. 164.0°-167.0° C.

Workup

  1. temperaturethe mixture was heated to 120° to 130° C. for 6 hours
  2. customAfter completion of the reaction
  3. temperaturethe mixture was cooled
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluent; ethyl acetate/hexane/chloroform=1:3:1)
  8. customAfter recrystallization from ether/chloroform

Sources & evidence

ORD record
ord-323522222ffb4e3fabe453fd3ecedb4a
Source dataset
uspto-grants-1997_07
Patent number
US05643911

Reaction notes

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