Diisopropylethylamine → methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate

HRID 241799ノート

反応式

HRID 241799 の反応式
Cl[CH:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl.[CH3:24][O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27]>C(#N)C.CCOC(C)=O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH:2]2[N:31]1[CH2:32][CH2:33][N:28]([C:26]([O:25][CH3:24])=[O:27])[CH2:29][CH2:30]1)([O-:13])=[O:12]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 18399648Methyl piperazine-1-carboxylate hydrochlorideHCID 593027291-chloro-4-nitro-2,3-dihydro-1H-indene

生成物 1

HCID 59302725methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate収率 78%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
79 °C

実験手順

To a room temperature solution of 1-Chloro-4-nitro-2,3-dihydro-1H-indene (221 mg, 1.12 mmol, 1.0 equiv) and DIPEA (430 μL, 2.46 mmol, 2.2 equiv) in dry acetonitrile (1.6 mL) was added methylpiperazine carboxylate hydrochloride salt (444 mg, 2.46 mmol, 2.2 equiv) as a solid in one portion. The resulting reaction mixture was heated to 79° C. overnight. The reaction mixture was allowed to cool to RT and diluted with EtOAc. The organic layer was extracted with 1 M HCl (3×20 mL), and the combined aqueous layers were treated with 3 N NaOH until the pH=10. The resulting solution was extracted three times with EtOAc, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a brown oil (239 mg, 78%). LCMS [M+H]+=306.1.

後処理

  1. customThe resulting reaction mixture
  2. temperatureto cool to RT
  3. extractionThe organic layer was extracted with 1 M HCl (3×20 mL)
  4. additionthe combined aqueous layers were treated with 3 N NaOH until the pH=10
  5. extractionThe resulting solution was extracted three times with EtOAc
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f6111a8b74104884ac40d923feb071c7
出典データセット
uspto-grants-2014_02
特許番号
US08653081B2

反応ノート

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