Methanol → 5-[N-(2-aminoethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole dihydrochloride

HRID 1637265ノート

反応式

HRID 1637265 の反応式
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=O)[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22].CO.C([BH3-])#N.[Na+].C(Cl)[Cl:31]>>[ClH:31].[ClH:31].[NH2:22][CH2:21][CH2:20][NH:23][CH:18]1[C:13]2[C:14]3[C:15](=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[NH:8][C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:16][CH2:17]1

参加物

6

反応物 5

HCID 887MethanolHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

生成物 1

HCID 193481885-[N-(2-aminoethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole dihydrochloride収率 32%

実験手順

A portion (0.20 g) of the compound obtained in Example 41 and ethylenediamine (0.54 ml) were suspended in a mixed solvent of methanol (3 ml) and methylene chloride (3 ml) and to the suspension was added sodium cyanoborohydride (61 mg). The mixture was stirred for 13 hours at room temperature and heated to reflux for further 20 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, followed by extraction with three portions of methylene chloride. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/methanol=19:1-9:1-4:1). The resulting brown foam was dissolved in a solution (3 ml) of 10% hydrochloric acid in methanol and the solution was concentrated. The concentrate was crystallized from ether to yield 93 mg (32%) of the titled compound as brown crystals.

後処理

  1. temperatureheated
  2. temperatureto reflux for further 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionfollowed by extraction with three portions of methylene chloride
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=19:1-9:1-4:1)
  10. dissolutionThe resulting brown foam was dissolved in a solution (3 ml) of 10% hydrochloric acid in methanol
  11. concentrationthe solution was concentrated
  12. customThe concentrate was crystallized from ether

出典と根拠

ORDレコード
ord-443e41afab3b405caa7810aa1af0f5ba
出典データセット
uspto-grants-2000_03
特許番号
US06040331

反応ノート

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