Ethanolamine → 5-[N-(2-hydroxyethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637264ノート

反応式

HRID 1637264 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.[NH2:20][CH2:21][CH2:22][OH:23].CO.C([BH3-])#N.[Na+]>C(Cl)Cl>[OH:23][CH2:22][CH2:21][NH:20][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 4

HCID 700EthanolamineHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

生成物 1

HCID 193482865-[N-(2-hydroxyethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole収率 32%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A portion (0.20 g) of the compound obtained in Example 41 and 2-aminoethanol (0.49 ml) were suspended in a mixed solvent of methanol (3 ml) and methylene chloride (2 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 8 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) and further crystallized from ether to yield 75 mg (32%) of the titled compound as yellowish brown crystals.

後処理

  1. temperatureheated
  2. temperatureto reflux for further 8 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)
  10. customfurther crystallized from ether

出典と根拠

ORDレコード
ord-42b03a779ff046ad8a67abe15fdaa0c7
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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