tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate → tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

HRID 604311Notes

Reaction equation

HRID 604311 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[N:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]#[N:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

Product 1

HCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Add 4-cyanomethylenepiperidine-1-carboxylic acid t-butyl ester (5.39 g, 24.25 mmol) in ethanol (160 mL) to a suspension of 5% palladium on charcoal (0.69 g) in ethanol (20 mL) and hydrogenate at room temperature with agitation at 60 psi for 6 hr. Filter the mixture through celite and evaporate the solvent in vacuo to give 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester as an oil which solidifies on standing to give a solid (5.43 g, 99.8%). MS (m/z): 247 (M+Na).

Workup

  1. filtrationFilter the mixture through celite
  2. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-2724c4bbb86a488a8ab4f6ca7bf613da
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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