Acetic Acid → 4-[1-(4-Aminobutyl)piperidin-4-yl]butyramide

HRID 1097291ノート

反応式

HRID 1097291 の反応式
O=C1C2C(C=CC=C2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:18][CH2:17]1.O.NN.C(O)(=O)C>C(O)C>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 668109714-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}-butyramide

生成物 1

HCID 668109774-[1-(4-Aminobutyl)piperidin-4-yl]butyramide収率 130.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Compound 4 (0.30 g, 0.76 mmol) was dissolved in ethanol (5 mL). To the solution was added hydrazine monohydrate (0.11 mL, 2.28 mmol) followed by a catalytic amount of acetic acid (0.1 mL). The mixture was heated to reflux for two hours, cooled to room temperature, and concentrated under vacuum. The resulting residue was subjected to column chromatography eluting with 0-20% (20:80 ammonium hydroxide/methanol) in dichloromethane to afford the desired product 5 (0.24 g, 80%) as a colorless, viscous oil: 1H NMR (500 MHz, CD3OD) δ 1.25 (m, 4H), 1.55 (m, 6H), 1.72 (m, 2H), 2.00 (m, 2H), 2.18 (m, 3H), 2.36 (t, 2H), 2.74 (t, 2H), 2.96 (d, 2H), 3.28 (br, 4H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for two hours
  3. concentrationconcentrated under vacuum
  4. washeluting with 0-20% (20:80 ammonium hydroxide/methanol) in dichloromethane

出典と根拠

ORDレコード
ord-2638c911c22a422f9465bb1e3e5b8faf
出典データセット
uspto-grants-2012_03
特許番号
US08143256B2

反応ノート

読み込み中…