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

HRID 1097291노트

반응식

HRID 1097291 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2638c911c22a422f9465bb1e3e5b8faf
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143256B2

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