乙醇 → 4-(1-Benzyl-piperidin-4-ylidenemethyl)-benzonitrile

HRID 1663236笔记

反应方程式

HRID 1663236 反应方程式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OP([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)(=O)OCC)C.CN(C)C=O.C(O)C>O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

6

反应物 4

HCID 702乙醇HCID 6228N,N-二甲基甲酰胺HCID 19220N-苄基哌啶酮HCID 241438(4-氰基苄基)亚磷酸二乙酯

产物 1

HCID 674356554-(1-Benzyl-piperidin-4-ylidenemethyl)-benzonitrile收率 87.7%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

Under argon, to a stirred mixture of N-benzyl-4-piperidone (Aldrich) (26.0 g, 0.137 mol) and (4-cyano-benzyl)-phosphonic acid diethyl ester (36.6 g, 0.1445 mol) in dimethylformamide (260 mL) sodium hydride (60%, 7.8 g, 0.195 mol) was added at 0° C. The reaction mixture was stirred at room temperature overnight, then ethanol (10 mL) was added dropwise, the so obtained mixture was poured into water (300 mL), and extracted with diethyl ether (3×300 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by column chromatography using Kieselgel 60 (0.040-0.063 mm) (Merck) as adsorbent, and n-hexane:ethyl acetate=2:1 as eluent to yield 34.65 g (87%) of the title compound as an oil.

后处理

  1. additionwas added at 0° C
  2. extractionextracted with diethyl ether (3×300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

来源与证据

ORD记录
ord-0e4b8fa593604101a6f0ea884a195f99
来源数据集
uspto-grants-2011_10
专利号
US08034827B2

反应笔记

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