Cyanoacetamide → HCID 178436607, compound

HRID 1854075Notes

Reaction equation

HRID 1854075 reaction equation
[CH3:1][C:2](=O)[C:3]#[C:4][CH2:5][CH3:6].[C:8]([CH2:10][C:11]([NH2:13])=[O:12])#[N:9].C(O)(=O)C.N1CCCCC1.N1CCCCC1>C(O)C.O.C(O)(=O)C>[CH2:5]([C:4]1[C:10]([C:8]#[N:9])=[C:11]([OH:12])[N:13]=[C:2]([CH3:1])[CH:3]=1)[CH3:6]

Participants

8

Reactant 4

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 1371513-Hexyn-2-oneHCID 9793820Piperidine, acetate

Product 1

HCID 178436607HCID 178436607, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of hex-3-yn-2-one (1.5 g, 15.6 mmol) in 90% ethanol (30 mL), cyanoacetamide (1.58 g, 18.72 mmol) and piperidine acetate {prepared by the addition of piperidine to a solution of acetic acid (0.258 mL) in water (0.65 mL) till pH 8} were added and reaction heated at 90° C. for 12 h. On completion, ethanol was evaporated and water was added to residue. Solid obtained was filtered and washed with water. Then this solid was stirred with acetonitrile for 10 min and filtered again to obtain the desired intermediate (1.5 g, 60%).

Workup

  1. additionwere added
  2. customreaction
  3. customOn completion, ethanol was evaporated
  4. additionwater was added to residue
  5. customSolid obtained
  6. filtrationwas filtered
  7. washwashed with water
  8. filtrationfiltered again

Sources & evidence

ORD record
ord-f78890a5e2674f678f84d6c6e022e1ee
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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