4-Toluenesulfonyl chloride → (1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

HRID 603181노트

반응식

HRID 603181 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10398044(1-Benzylpiperidin-3-yl)methanol

생성물 1

HCID 57656889(1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate수율 80.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1-benzylpiperidin-3-yl)methanol (820 mg) and triethylamine (0.84 mL) in dichloromethane (10 mL) was added para-toluenesulfonyl chloride (846 mg). The solution was stirred overnight at room temperature. The mixture was partitioned between dichloromethane and water. The layers were separated and the organic layer was dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 50% ethyl acetate in hexane to give the title compound as a colourless oil (1.15 g, 80%).

후처리

  1. customThe mixture was partitioned between dichloromethane and water
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ad10acc96531417f85b45d2bffc02a5d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906645B2

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