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Cyclopropylamine → N1-cyclopropyl-N4-(5-isoquinolyl)-1,4-cyclohexanediamine

HRID 1352167
ノート
印刷プレビュー

反応式

HRID 1352167 の反応式
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][CH:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CO>CO>[CH:19]1([NH:22][CH:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)[CH2:13][CH2:14]2)[CH2:21][CH2:20]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178381944-(5-Isoquinolylamino)-1-cyclohexanone2 回HCID 21893726Hydrochloride methanol

生成物 1

HCID 9835432N1-cyclopropyl-N4-(5-isoquinolyl)-1,4-cyclohexanediamine収率 15.7%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

4-(5-Isoquinolylamino)-1-cyclohexanone (intermediate 4) (60 mg) and cyclopropylamine (30 mg) were dissolved in methanol (1 ml), and sodium triacetoxyborohydride (105 mg) was added by portions to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. Hydrochloric acid-methanol was then added thereto, and the reaction mixture was. stirred and was then concentrated. The residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions containing respective compounds, followed by extraction with chloroform-propanol (3/1). The organic layers were dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure to give an anti-form compound (11 mg) and a syn-form compound (12 mg).

後処理

  1. stirringstirred
  2. concentrationwas then concentrated
  3. customThe residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]
  4. additionA saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions
  5. additioncontaining respective compounds
  6. extractionfollowed by extraction with chloroform-propanol (3/1)
  7. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under the reduced pressure

出典と根拠

ORDレコード
ord-d40f007530664318aed17527ba5aa410
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07217722B2

反応ノート

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