Ethyl cyanoacetate → 4-(Cyanoacetyl)morpholine

HRID 2114025Notes

Reaction equation

HRID 2114025 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O:9][C:10](=O)[CH2:11][C:12]#[N:13])C>C(OCC)(=O)C>[C:12]([CH2:11][C:10]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:9])#[N:13]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 8083Morpholine

Product 1

HCID 2292794-(Cyanoacetyl)morpholineYield 701.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A 4-neck 500 mL flask was charged with morpholine (77.0 g, 0.088 mol). Ethylcyanoacetate (100.0 g, 0.088 mol) was added. After addition, the reaction mixture was stirred. The mixture progressively turned yellow to clear. The mixture was heated to 100 to 110° C. for 3.0 hours. A solid formed after cooling to room temperature. Ethyl acetate (150 ml) and heptanes (300 ml) were added and the mixture stirred for 30 minutes at room temperature. The solid was filtered to give 95.2 g (71% yield) of 4-cyanoacetylmorpholine. 1H NMR: δ (DMSO-d6) 4.02 (s, 2H); 3.37 (m, 2H); 3.55 (m, 4H); 3.45 (m, 2H).

Workup

  1. additionAfter addition
  2. customA solid formed
  3. temperatureafter cooling to room temperature
  4. stirringthe mixture stirred for 30 minutes at room temperature
  5. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-712b020846c34f6ba6e71ab8db646f42
Source dataset
uspto-grants-2008_10
Patent number
US07432377B2

Reaction notes

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