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Water → 1,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol

HRID 66108
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인쇄 미리보기

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HRID 66108 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[CH2:17][CH2:16]1.O.[OH-].[Na+]>CCOCC>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]2[OH:32])[CH2:17][CH2:16]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 122701533,4-Dihydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1(2H)-naphthalenoneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 227555621,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol수율 95.5%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매
2회

실험 절차

To a slurry of 0.54 g of lithium aluminum hydride in ether is added a solution of 3,4-dihydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1(2H)-naphthalenone (5.0 g, prepared as described in Example 1A) in 150 ml of warm ether. The resulting mixture is refluxed under a nitrogen atmosphere for 3 hours, cooled in ice, and treated (in order) with 0.55 ml of water, 0.55 ml of 15% sodium hydroxide solution and 1.65 ml of water. This mixture is stirred at room temperature for 30 minutes and the inorganic precipitates removed by filtration. The ether solution is dried over anhydrous sodium sulfate, concentrated in vacuo, and triturated with 1:1 hexane-ether to yield 4.8 g of 1,2,3,4-tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol. One crystallization of this material from cyclohexane yields the trans isomer in pure form as determined by NMR and thin layer chromatography analysis.

후처리

  1. temperatureThe resulting mixture is refluxed under a nitrogen atmosphere for 3 hours
  2. temperaturecooled in ice
  3. customthe inorganic precipitates
  4. customremoved by filtration
  5. dry with materialThe ether solution is dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customtriturated with 1:1 hexane-ether

출처 및 근거

ORD 기록
ord-60d7759d036e44869b0ce08005c19806
출처 데이터셋
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04130646

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