1-Methylpiperazine → 1-Methyl-4-({(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl)piperazine

HRID 853913노트

반응식

HRID 853913 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])(=O)=O)=CC=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOCC>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[CH2:31][CH2:30]1

참가 물질

6

반응물 3

HCID 531671-MethylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10905672{(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl 4-methylbenzenesulfonate

생성물 1

HCID 589325581-Methyl-4-({(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl)piperazine수율 55%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

반응 조건

온도
140 °C

실험 절차

To a solution of {(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl 4-methylbenzenesulfonate (9.427 g, 23.13 mmol) (Tetrahedron, 43(14), 3289, 1987) in toluene (150 mL), was added n-methyl-piperazine (12.8 mL, 115.65 mmol) and DBU (0.352 g, 2.313 mmol) and the solution was stirred at 140° C. overnight. The reaction was then diluted with ether and washed with brine. The organic layer was dried over Na2SO4, filtered, concentrated and purified on Biotage flash 40M cartridge silica gel eluting with CH2Cl2/CH3OH/NH4OH (95.5/3/1.5) to give an off white solid (2.570 g, 55% ). NMR (400 Mz, DMSO-d6): consistent. MS (ES+) m/z 338.1 [M+H]. m.p.: 96.5-97.7° C. Reference: (Tetrahedron, 43(14), 3289, 1987).

후처리

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on Biotage flash 40M cartridge silica gel eluting with CH2Cl2/CH3OH/NH4OH (95.5/3/1.5)

출처 및 근거

ORD 기록
ord-fef5cb0c18be48b29be5920d6bae3773
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256198B2

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