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

HRID 885841Notes

Reaction equation

HRID 885841 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 670503194-(1-Methyl-piperidin-4-ylidenemethyl)-benzonitrileYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-08cb25ab19484f61829bed6437d5dfa6
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

Loading…