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

HRID 473816ノート

反応式

HRID 473816 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-80e881508e534ff1bce91a395aef24fb
出典データセット
uspto-grants-2014_01
特許番号
US08637499B2

反応ノート

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