Benzyl chloroformate → 1-Benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate

HRID 473816노트

반응식

HRID 473816 반응식
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C(N(C(C)C)CC)(C)C>O1CCOCC1.C(OCC)(=O)C>[C:1]1([CH:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][N:12]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 2735358Tert-butyl 3-phenylpiperazine-1-carboxylate

생성물 1

HCID 675145701-Benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate수율 59%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A solution of tert-butyl 3-phenylpiperazine-1-carboxylate (0.95 g, 3.6 mmol), benzyl chloroformate (0.85 g, 5.0 mmol) and diisopropylethylamine (1.0 g, 7.7 mmol) in dioxane (20 mL) was heated to 95° C. for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL). After drying over anhydrous sodium sulfate, filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to give 1-benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate (0.84 g, 59% yield).

후처리

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL)
  3. dry with materialAfter drying over anhydrous sodium sulfate, filtration and concentration
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8)

출처 및 근거

ORD 기록
ord-80e881508e534ff1bce91a395aef24fb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637499B2

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