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Formic Acid → HCID 22392274, compound

HRID 1358171
Notes
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Reaction equation

HRID 1358171 reaction equation
C=O.[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[C:7]1=[O:16].[CH:17](O)=O.[OH-].[Na+]>C(O)(CC)(C)C.O.C1(C)C=CC=CC=1>[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][C:10]([CH3:12])([CH3:13])[N:9]([CH3:17])[C:8]([CH3:15])([CH3:14])[C:7]1=[O:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 21951121HCID 21951121, compound

Product 1

HCID 22392274HCID 22392274, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×
HCID 1140
Toluene
Solvent
HCID 64052-Methyl-2-butanolSolvent2×

Conditions

Temperature
80 °C

Procedure

24.3 g (0.78 mol) of paraformaldehyde are added to a solution of 120 g (0.6 mol) of 1-(2-hydroxyethyl)-3,3,5,5-tetramethylpiperazin-2-one in 300 ml of tert-amyl alcohol. The mixture is then heated to 80° C. and 35.8 g (0.78 mol) of formic acid dissolved in 30 ml of tert-amyl alcohol are slowly added. Then, the mixture is maintained at 80° C. for further 1 hour and cooled to 50° C. Subsequently, 250 ml of toluene and 100 ml of water are added. The mixture is then stirred and 33 g (0.825 mol) of sodium hydroxide dissolved in 60 ml of water are slowly added. The organic phase is separated, washed with water, dried over anhydrous sodium sulfate, filtered and evaporated under vacuum (60° C./10 mbar). A white solid with a melting point of 77°-80° C. is obtained.

Workup

  1. additionare slowly added
  2. temperatureThen, the mixture is maintained at 80° C. for further 1 hour
  3. temperaturecooled to 50° C
  4. additionare slowly added
  5. customThe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum (60° C./10 mbar)
  10. customA white solid with a melting point of 77°-80° C. is obtained

Sources & evidence

ORD record
ord-d57e964a13aa4eb9be8c74a42e16f220
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06596461B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes