Cyanoacetamide → HCID 178442849, compound

HRID 1159744Notes

Reaction equation

HRID 1159744 reaction equation
C(O[C:4](=[O:24])[CH2:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])C.[C:25]([CH2:27][C:28]([NH2:30])=[O:29])#[N:26].N1CCCCC1>CO>[C:25]([C:27]1[C:28]([OH:29])=[N:30][C:4]([OH:24])=[CH:5][C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])#[N:26]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 86044196HCID 86044196, compound

Product 1

HCID 178442849HCID 178442849, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Oxo-nonadecanoic acid ethyl ester (11.3 mmol), cyanoacetamide (0.95 g, 11.3 mmol) and piperidine (0.95 g, 11.3 mmol) in MeOH (3 mL) were heated under reflux for 24 h. The solvent was evaporated, and the residue was dissolved in hot water. The product was precipitated by addition of concentrated HCl, filtered, washed with ice water and CHCl3 and dried in vaccum to give 3-cyano-2,6-dihydroxy-4-hexadecyl-pyridine as a white powder. Yield: 40%. Anal. C22H36N2O2: Calcd: C, 73.29; H, 10.06; N, 7.77; O, 8.88. Found: C, 73.35; H, 10.12; N, 7.85; O, 8.97. MS (ESIMS): m/z: 360.3.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in hot water
  4. customThe product was precipitated by addition of concentrated HCl
  5. filtrationfiltered
  6. washwashed with ice water and CHCl3
  7. customdried in vaccum

Sources & evidence

ORD record
ord-8418ee3c03b9441597e230778f4a59a8
Source dataset
uspto-grants-2010_10
Patent number
US07812251B2

Reaction notes

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