Acrylonitrile → Ethyl 1-(2-cyanoethyl)piperidine-4-carboxylate

HRID 456590Notes

Reaction equation

HRID 456590 reaction equation
C([N:3]1CC[CH:6](C(O)=O)[CH2:5][CH2:4]1)C.[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13].C(#N)C=C>C(O)(C)C>[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([CH2:6][CH2:5][C:4]#[N:3])[CH2:19][CH2:18]1)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 86594498Piperidine-4-carboxylic acid ethyl ester (ethylisonipecotate)

Product 1

HCID 43084552Ethyl 1-(2-cyanoethyl)piperidine-4-carboxylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of piperidine-4-carboxylic acid ethyl ester (ethylisonipecotate) (4.7 g, 30 mmol), acrylonitrile (1.7 g, 31 mmol) in isopropyl alcohol (30 ml) was stirred at room temperature for 15 hours, then evaporated to dryness to afford 1-(2-cyano-ethyl)-piperidine-4-carboxylic acid ethyl ester as an oil (6.4 g, 100%).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-7524ec68f1c04433b6e1f6aa8924b0bb
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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