Diisopropylethylamine → 1-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazine

HRID 417872ノート

反応式

HRID 417872 の反応式
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:6]([N:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH2:18][CH2:19]1)[CH2:7][CH2:8][C:9]#[CH:10]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 12476209Pent-4-yn-1-yl methanesulfonate

生成物 1

HCID 866082261-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazine収率 71.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of pent-4-ynyl methanesulfonate (1.05 g), 1-(pyridin-2-yl)piperazine (1.02 g) and diisoproylethylamine (1.2 ml) in THF (5 mL) was heated to reflux overnight. The mixture was concentrated, diluted with aq. NaOH 2M (10 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0) afforded 1-(pent-4-ynyl)-4-(pyridin-2-yl)piperazine (1.02 g).

後処理

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with aq. NaOH 2M (10 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0)

出典と根拠

ORDレコード
ord-791930dec88444d59133098cfe71570c
出典データセット
uspto-grants-2012_01
特許番号
US08093229B2

反応ノート

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