Sodium amide → 1-[3-Cyano-3,3-bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazine

HRID 2181635노트

반응식

HRID 2181635 반응식
[NH2-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:10]#[N:11].Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1>COCCOC.O>[C:10]([C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:25][CH2:26]1)#[N:11]

참가 물질

6

반응물 3

HCID 24533Sodium amideHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazineHCID 140060572,2-Bis-(2-pyridyl)acetonitrile

생성물 1

HCID 224821111-[3-Cyano-3,3-bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazine수율 68.4%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매3회

실험 절차

To a suspension of 0.21 g of 95% sodium amide in 2 mL of 1,2-dimethoxyethane was added dropwise a solution of 0.78 g of 2,2-bis-(2-pyridyl)acetonitrile (prepared as described in Heterocycles 1995, 40, 757) in 8 mL of 1,2-dimethoxyethane, with stirring under a nitrogen atmosphere at room temperature. After 1 h, there were added dropwise, 1.02 g of 1-(2-chloroethyl)-4-(2-methoxy-phenyl)piperazine dissolved in 4 mL of 1,2-dimethoxyethane. The resultant reaction mixture was then refluxed for 20 h, followed by cooling to room temperature, and was then poured cautiously into 40 g of ice, diluted with water, and extracted with ethyl acetate. The combined organic phases were then washed with water, dried on sodium sulphate, and then evaporated thoroughly under vacuum. The obtained crude was then purified by flash chromatography (ethyl acetate-methanol gradient from 10:0 to 9:1). The recovered fractions were then evaporated to complete dryness, affording 1.13 g of the title product (68.4%).

후처리

  1. additionthere were added dropwise
  2. customThe resultant reaction mixture
  3. temperaturewas then refluxed for 20 h
  4. temperatureby cooling to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases were then washed with water
  7. customdried on sodium sulphate
  8. customevaporated thoroughly under vacuum
  9. customThe obtained crude
  10. customwas then purified by flash chromatography (ethyl acetate-methanol gradient from 10:0 to 9:1)
  11. customThe recovered fractions were then evaporated

출처 및 근거

ORD 기록
ord-73501f0331dd48a8939dfbf41a4012d4
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894052B1

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