Formic Acid → HCID 22392274, compound

HRID 1358171Notes

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]

Participants

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

additionare slowly added
temperatureThen, the mixture is maintained at 80° C. for further 1 hour
temperaturecooled to 50° C
additionare slowly added
customThe organic phase is separated
washwashed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under vacuum (60° C./10 mbar)
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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