Sodium hydride → 4-(1-Methyl-piperidin-4-ylidenemethyl)-benzonitrile

HRID 885841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885841
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.C(OP([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)(=O)OCC)C.[H-].[Na+]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 740491-Methyl-4-piperidoneHCID 241438Diethyl (4-Cyanobenzyl)phosphonate

Produkt 1

HCID 670503194-(1-Methyl-piperidin-4-ylidenemethyl)-benzonitrileAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1-Methyl-piperidin-4-one (500 mg, 4.42 mmol) was dissolved in THF (10 ml) and added dropwise to a stirred mixture of (4-cyano-benzyl)-phosphonic acid diethyl ester (1.12 g, 4.42 mmol) and NaH (60% oil dispersion, 212 mg, 5.30 mmol) in THF (10 ml) under N2. The solution was stirred at room temperature for 2 h, then partitioned between water and AcOEt. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by silica gel chromatography (DCM/MeOH/NH4OH 95:5:0.2). The collected fractions gave 392 mg of 4-(1-methyl-piperidin-4-ylidenemethyl)-benzonitrile as a yellow oil.

Aufarbeitung

  1. custompartitioned between water and AcOEt
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by silica gel chromatography (DCM/MeOH/NH4OH 95:5:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-08cb25ab19484f61829bed6437d5dfa6
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242175B2

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