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Sodium borohydride → 2,3-Dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-ol

HRID 66110
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HRID 66110 반응식
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH:8]([CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]1)[CH2:7]2.[BH4-].[Na+]>CO.O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([OH:15])[CH:8]([CH2:16][N:17]1[CH2:18][CH2:19][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:21][CH2:22]1)[CH2:7]2
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참가 물질

5

반응물 2

HCID 4311764Sodium borohydride3회HCID 131711376HCID 131711376, 화합물

생성물 1

HCID 227555592,3-Dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-ol수율 50.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매3회

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온도
0 °C

실험 절차

A suspension of 4.9 g of 2,3-dihydro-5,6-dimethoxy-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1H-inden-1-one, hydrochloride in 100 ml of methanol is cooled to 0° C. and treated with a solution of 1.52 g of sodium borohydride in 10 ml of water (the sodium borohydride is added dropwise). The mixture is stirred at room temperature overnight followed by the addition of an additional 1.52 g of sodium borohydride in 10 ml of water at 0° C. The mixture is stirred for an additional 2 hours at room temperature. The reaction mixture is chilled to 0° C. and treated with 30 ml of water. After 30 minutes at 0° C., the solvents are removed in vacuo, and the residue is distributed between dichloromethane and water. The organic layer is dried with sodium sulfate and evaporated in vacuo to a foamy residue (4.1 g). The residue is dissolved in a small amount of dichloromethane and chromatographed on a 150 g-Activity III neutral alumina column using ethyl acetate/hexane (3:1) in 50 ml fractions (a total of 500 ml). After evaporation of the combined fractions there is 2.7 g of residue. Trituration with pentane gives 2.28 g of an amorphous solid with indeterminant melting point. Crystallization from ethyl acetate/pentane yields 1.80 g of the title compound, melting point 109.5°-111.5° C.

후처리

  1. additionis added dropwise)
  2. stirringThe mixture is stirred for an additional 2 hours at room temperature
  3. temperatureThe reaction mixture is chilled to 0° C.
  4. waitAfter 30 minutes at 0° C.
  5. customthe solvents are removed in vacuo
  6. dry with materialThe organic layer is dried with sodium sulfate
  7. customevaporated in vacuo to a foamy residue (4.1 g)
  8. dissolutionThe residue is dissolved in a small amount of dichloromethane
  9. customchromatographed on a 150 g-Activity III neutral alumina column
  10. customAfter evaporation of the combined fractions there

출처 및 근거

ORD 기록
ord-cd9bb0346c3c41079aad7966c1067ed1
출처 데이터셋
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04130646

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