Sodium Hydroxide → HCID 54014973, compound

HRID 2211102Notes

Reaction equation

HRID 2211102 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:16]=[CH:15][S:14][CH:13]=2)=[N:4][N:3]=1.[OH-].[Na+]>CN1CCCC1=O>[C:6]1([C@H:5]([NH:4][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:16]=[CH:15][S:14][CH:13]=3)=[N:4][N:3]=2)[CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19375606HCID 19375606, compound

Product 1

HCID 54014973HCID 54014973, compoundYield 143.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

510 mg of 1-chloro-4-(3-thienyl)phthalazine and 790 mg of D-α-phenylethylamine were dissolved in 2 ml of N-methylpyrrolidone, and the solution was stirred at 140° C. for 6 hours. After cooling the solution, an aqueous 5% NaOH solution was added to the solution, and the resultant solution was extracted with chloroform. The organic layer was dried, concentrated, purified by silica gel chromatography (eluent: hexane, chloroform, ethyl acetate), and recrystallized from ether to obtain 492 mg of (R)-1-(α-phenylethylamino) -4-(3-thienyl)phthalazine.

Workup

  1. temperatureAfter cooling the solution
  2. extractionthe resultant solution was extracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (eluent: hexane, chloroform, ethyl acetate)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-7dca298d17da49f081ac02d8feb8143a
Source dataset
uspto-grants-1995_10
Patent number
US05462941

Reaction notes

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