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

HRID 1663236노트

반응식

HRID 1663236 반응식
[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

참가 물질

6

반응물 4

HCID 702EthanolHCID 6228DimethylformamideHCID 192201-Benzyl-4-piperidoneHCID 241438Diethyl (4-Cyanobenzyl)phosphonate

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e4b8fa593604101a6f0ea884a195f99
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034827B2

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