Cyanoacetamide → 3-(Aminomethyl)-5-fluoro-4,6-dimethyl-2(1H)-pyridinone

HRID 1522517Notes

Reaction equation

HRID 1522517 reaction equation
[F:1][CH:2]([C:6](=O)[CH3:7])[C:3](=O)[CH3:4].[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].N1CCCCC1>CCO>[NH2:10][CH2:9][C:11]1[C:12](=[O:13])[NH:14][C:3]([CH3:4])=[C:2]([F:1])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 116266523-Fluoropentane-2,4-dione

Product 1

HCID 671242643-(Aminomethyl)-5-fluoro-4,6-dimethyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-fluoro-2,4-pentanedione (247 mg, 2.10 mmol), cyanoacetamide (176 mg, 2.1 mmol, 1 equiv) and piperidine (0.21 mL, 2.1 mmol, 1 equiv) in 3 mL of EtOH was heated at 85° C. for 16 h, resulting in a clear but dark brown solution. The mixture was concentrated in vacuo. The residue was taken up in 2 mL of 1N HCl to give a suspension, which was filtered. The tan solids collected were dried under vacuum to give the desired product as 80 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.33 (s, 3H), 2.42 (s, 3H).

Workup

  1. customresulting in a clear but dark brown solution
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a suspension, which
  4. filtrationwas filtered
  5. customThe tan solids collected
  6. customwere dried under vacuum

Sources & evidence

ORD record
ord-2654bcace64b4f5f979eb27a2c627f3e
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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