Formic Acid → HCID 20512078, compound

HRID 1164386Notes

Reaction equation

HRID 1164386 reaction equation
[CH2:1]([N:4]([CH2:17][CH:18]=[CH2:19])[C:5]([CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].[CH:20](O)=O.[OH-].[Na+]>C=O>[CH2:17]([N:4]([CH2:1][CH:2]=[CH2:3])[C:5]([CH:7]1[CH2:8][C:9]([CH3:16])([CH3:15])[N:10]([CH3:20])[C:11]([CH3:13])([CH3:14])[CH2:12]1)=[O:6])[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 20512083HCID 20512083, compound

Product 1

HCID 20512078HCID 20512078, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

4-[(Diallylamino)carbonyl]-2,2,6,6-tetramethylpiperidine (58.0 grams; 0.219 mole) is slurried in 37% formaldehyde (98.6 mls) at room temperature and 95% formic acid (17.4 mls) is added thereto. The mixture is heated at reflux for 18 hours and the resulting two-phase reaction mixture is adjusted to pH 11-12 by adding 50% sodium hydroxide. The mixture is extracted with dichloromethane and the organic extracts are combined and evaporated to obtain a clear liquid which on distillation affords 58.3 grams of the desired product which boils at 118°-125° C. at 0.10-0.15 mm of mercury.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hours
  3. customthe resulting two-phase reaction mixture
  4. extractionThe mixture is extracted with dichloromethane
  5. customevaporated
  6. customto obtain a clear liquid which
  7. distillationon distillation

Sources & evidence

ORD record
ord-89cd60b5ea894b41a9dd1a180b2f5881
Source dataset
uspto-grants-1983_01
Patent number
US04369274

Reaction notes

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