Ethyl chloroacetate → HCID 15034768, compound

HRID 1170869Notes

Reaction equation

HRID 1170869 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[N:7][C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(#N)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[N:7][C:8]#[N:9])[CH3:22]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetate2×HCID 11430Potassium CarbonateHCID 178512034HCID 178512034, compound

Product 1

HCID 15034768HCID 15034768, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

Piperidin-2-ylidene-cyanamide (C) (9.67 g, 78.5 mmol) was dissolved in acetonitrile (150 mL) under a low heat. Potassium carbonate (13.0 g, 94.2 mmol, 1.2 eq.) and Ethyl chloroacetate (11.7 mL, 109.9 mmol, 1.4 eq.) were then added thereto and the resulting suspension was heated for 16 hours at 85° C. A further amount of ethyl chloroacetate (1.67 mL, 15.7 mmol, 0.2 eq.) was then added. The reaction mixture was heated under reflux for 6 hours. The cooled suspension was then filtered and the solid residue was washed with DCM. The filtrate was reduced under vacuum and, after column chromatographic purification (SiO2, heptane/EtOAc 2:3), 16.16 g (98%) of the desired product (2-cyanoimino-piperidin-1-yl)-acetic acid ethyl ester (D) was obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 hours
  3. filtrationThe cooled suspension was then filtered
  4. washthe solid residue was washed with DCM
  5. customafter column chromatographic purification (SiO2, heptane/EtOAc 2:3)

Sources & evidence

ORD record
ord-89b9bb45d1f44282b76cbfb547d40a95
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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