1-Phenethylamine, (-)- → (S)-1-(1-Phenylethylamino)-4-(4-pyridylmethyl)phthalazine

HRID 49863

Reaktionsgleichung

Reaktionsgleichung von HRID 49863
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[C:19]1([C@@H:25]([NH2:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)CCC>[C:19]1([C@@H:25]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 758181-Phenethylamine, (-)-HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Produkt 1

HCID 54550094(S)-1-(1-Phenylethylamino)-4-(4-pyridylmethyl)phthalazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 0.511 g (2 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 1.273 ml (10 mmol) (S)-1 phenylethylamine and 5 ml 1-butanol is stirred for 24 h at 110° C. The reaction mixture is evaporated under vacuum and the residue distributed between dichloromethane and 20% aqueous potassium carbonate solution. The organic phase dried over anhydrous sodium sulfate is evaporated in the RE and then under HV and the residue purified on silica gel by flash chromatography using dichloromethane/methanol (50:1). The product-containing fractions are dissolved in 5 ml methanol, acidified with 0.75 ml 3N methanolic HCl and evaporated under vacuum. After recrystallization of the residue from methanol/acetonitrile, drying of the crystallizate under HV (8 h, 100° C.) and equilibration for 15 h at 20° C. and in room atmosphere, title compound is obtained with a water content of 10.66%; m.p. 190° C. (decomp.); ESI-MS: (M+H)+=341; [α]D20 =+42.1±0.8° (c=1.272%, methanol).

Aufarbeitung

  1. customThe reaction mixture is evaporated under vacuum
  2. dry with materialThe organic phase dried over anhydrous sodium sulfate
  3. customis evaporated in the RE
  4. customunder HV and the residue purified on silica gel by flash chromatography
  5. dissolutionThe product-containing fractions are dissolved in 5 ml methanol
  6. customevaporated under vacuum
  7. customAfter recrystallization of the residue from methanol/acetonitrile
  8. customdrying of the crystallizate under HV (8 h, 100° C.) and equilibration for 15 h at 20° C. and in room atmosphere

Quellen und Nachweise

ORD-Eintrag
ord-aba9693d37aa4c728072a9adba9d472f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710047B2

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