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

HRID 1384101ノート

反応式

HRID 1384101 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of 0.511 g (2 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 1.273 ml (10 mmol) (S)-1phenylethylamine 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 dichioromethane/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; [a]D20=+42.1±0.8° (c=1.272%, methanol).

後処理

  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

出典と根拠

ORDレコード
ord-aa0bced2a88945659d28d94e248153e6
出典データセット
uspto-grants-2001_07
特許番号
US06258812B1

反応ノート

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