Acetic Acid → N-(1-azabicyclo[2.2.2]oct-3 yl)-N'-(3-chlorphenyl)-1,2-diaminoethane

HRID 1609484

反応式

HRID 1609484 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][CH:7]=1.Cl.[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C:15](=O)[CH2:14]2.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]([NH:11][CH2:10][CH2:9][NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:14]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 11008376N1-(3-chlorophenyl)ethane-1,2-diamine

生成物 1

HCID 10492977N-(1-azabicyclo[2.2.2]oct-3 yl)-N'-(3-chlorphenyl)-1,2-diaminoethane収率 40.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of N-(3-chlorophenyl)-1,2-diaminoethane (1 g; 0.00586 moles) in 25 ml of anhydrous methanol kept under nitrogen atmosphere, 3-quinuclidinone hydrochloride (1.01 g, 0.00627 moles) is added. The pH is adjusted to pH 6 by addition of glacial acetic acid. Sodium cyanoborohydride (0.74 g; 0.0117 moles) is added in two portions. The reaction mixture is refluxed for 10 hours, cooled and then filtered. After evaporation to dryness the residue is taken up with water, basified with 20% sodium hydroxide solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate and, after filtration, evaporated to dryness. The residue is purified by silica gel flash-chromatography (methylene chloride-methanol30% ammonium hydroxide, 1.50:50:5 as eluant) to give the desired product as a clear oil (0.66 g).

後処理

  1. temperatureThe reaction mixture is refluxed for 10 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customAfter evaporation to dryness the residue
  5. extractionextracted three times with ethyl acetate
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationafter filtration
  9. customevaporated to dryness
  10. customThe residue is purified by silica gel flash-chromatography (methylene chloride-methanol30% ammonium hydroxide, 1.50:50:5 as eluant)

出典と根拠

ORDレコード
ord-a64f5decd6194bda933578a1707e7a43
出典データセット
uspto-grants-1995_03
特許番号
US05401750

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