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Water → (E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrile

HRID 54552
Notes
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Reaction equation

HRID 54552 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([CH2:18]P(=O)(OCC)OCC)#[N:17].[H-].[Na+].O>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:18]/[C:16]#[N:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 895841-Benzylpiperidine-4-carbaldehyde

Product 1

HCID 19959219(E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrileYield 109.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of 1-benzyl-4-formylpiperidine (4.5 g) in tetrahydrofuran (20 ml) was added dropwise to a suspension of diethyl cyanomethylphosphonate (4.31 g) and sodium hydride (0.97 g, 60% suspension in oil) in tetrahydrofuran (30 ml) at 0° C. under stirring. After stirring for 1 hour at ambient temperature, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine and dried over magnesium sulfate, and evaporated in vacuo to give (E)-3-(1-benzylpiperidin-4-yl)-2-propenenitrile (5.5 g) as an oil.

Workup

  1. stirringAfter stirring for 1 hour at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-24d05c94f6b3425fbf94f5419890062f
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05622976

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes