Ethyl cyanoacetate → 4-(Cyanoacetyl)morpholine

HRID 1726003Notes

Reaction equation

HRID 1726003 reaction equation
[C:1]([CH2:3][C:4](OCC)=[O:5])#[N:2].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>>[N:9]1([C:4](=[O:5])[CH2:3][C:1]#[N:2])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 8083Morpholine

Product 1

HCID 2292794-(Cyanoacetyl)morpholineYield 76.9%

Procedure

Ethyl cyanoacetate (5.33 mL, 50 mmol) and morpholine (17.49 mL, 0.2 mol) were gently refluxed at 90° C. in an oil bath for 2 days. The mixture was concentrated and the residue was purified by silica gel column chromatography eluting with 50% acetone in n-hexane. 5.93 g of the compound was obtained. MS (DCI) m/e 155 (M+H)+, 172 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 4.03 (s, 2H), 3.53-3.59 (m, 4H), 3.42-3.45 (m, 2H), 3.32-3.35 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with 50% acetone in n-hexane

Sources & evidence

ORD record
ord-48eeeb6f6feb41e6bd93109f58814a1a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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