Piperazine → 1-(2,3-Dihydro-benzofuran-2-ylmethyl)-piperazine

HRID 1772218ノート

反応式

HRID 1772218 の反応式
I[CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(#N)C>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH2:7][CH:3]1[CH2:2][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

参加物

5

反応物 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 3255132-(Iodomethyl)-2,3-dihydro-1-benzofuran

生成物 1

HCID 31596641-(2,3-Dihydro-benzofuran-2-ylmethyl)-piperazine収率 54%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-(iodomethyl)-2,3-dihydro-1-benzofuran (5.3 g, 20.4 mmol) in acetonitrile (70 ml) was added potassium carbonate (5.6 g, 40.5 mmol, 2 eq) and piperazine (8.8 g, 102.2 mmol, 5 eq). The resulting mixture was heated at reflux for 2 hours. The solids were then filtered off and the filtrate was concentrated under vacuum. The crude material was purified by silica gel chromatography using 0.5-2.5% methanol in dichloromethane to elute. The product-containing fractions were combined and concentrated under vacuum to afford 1-(2,3-dihydro-1-benzofuran-2-ylmethyl)piperazine as brown oil (2.4 g, 54%); (ES, m/z): [M+H]+ 219; 1H NMR (300 MHz, CDCl3): δ 7.07-7.17 (m, 2H), 6.78-6.85 (m, 2H), 4.92-5.01 (m, 1H), 3.22 (dd, J=9.0 Hz, 15.6 Hz, 1H), 2.91-2.99 (m, 4H), 2.71-2.82 (m, 1H), 2.53-2.71 (m, 6H).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe solids were then filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude material was purified by silica gel chromatography
  6. washto elute
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-f5d1171d16f7463c968d1fad145c89e9
出典データセット
uspto-grants-2016_02
特許番号
US09249102B2

反応ノート

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