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Benzaldehyde → 1-Benzyl-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine

HRID 748804
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HRID 748804 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CO.ClCCl.C(OCC)C>[CH2:33]([N:15]1[CH2:16][CH2:17][C:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)(=[O:10])=[O:11])([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:13][CH2:14]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 692029464-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine Hydrochloride

생성물 1

HCID 597507261-Benzyl-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine
수율 77.6%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine hydrochloride (100 mg, 0.245 mmol) obtained in Example 260, triethylamine (0.070 ml, 0.50 mmol) and benzaldehyde (0.050 ml, 0.428 mmol) were added to dichloromethane (5 ml), followed by the addition of sodium triacetoxyborohydride (110 mg, 0.500 mmol) at room temperature. The resulting mixture was stirred at room temperature for 14 hours. A 1N aqueous sodium hydroxide solution (3.0 ml) was then added. The resulting mixture was stirred at room temperature for 30 minutes. After diethyl ether was added, the resulting mixture was washed with a 1N aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the dichloromethane:methanol=50:1 eluate was concentrated under reduced pressure, whereby the title compound (87 mg, 0.19 mmol, 77%) was obtained as a white foam.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. washthe resulting mixture was washed with a 1N aqueous sodium hydroxide solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-29d67c405595431d8ef396e501be29fc
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07399775B2

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