Formaldehyde → HCID 86744898, compound

HRID 1198145Notes

Reaction equation

HRID 1198145 reaction equation
P([O-])(O)(O)=O.[Na+].[O:7]([CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[N+:8]([O-:10])=[O:9].C=O.[C:21](=O)([O-])[O-].[K+].[K+].[C:27]([O-:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([O-:32])=[O:31]>O1CCOCC1>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH3:21][N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][O:7][N+:8]([O-:10])=[O:9])[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 1254024-(2-Nitroxyethyl)piperidineHCID 5460307FumarateHCID 23672064Monosodium phosphate

Product 1

HCID 86744898HCID 86744898, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 100 ml. of a 1N solution of monosodium dihydrogen phosphate are added 3.4 g. (0.02 mole) 4-(2-nitroxyethyl)-piperidine in 10 ml. dioxan. While cooling and stirring, there are now added dropwise at +10° C., 10 ml. of a 37% solution of formaldehyde in the course of 10 minutes. After stirring overnight at ambient temperature, the reaction mixture is rendered alkaline with potassium carbonate and extracted with ethyl acetate. The organic phase is dried with anhydrous sodium sulphate and distilled in a vacuum. The remaining oil is dissolved in ethanol and converted into the salt by the addition of 1.2 g. fumaric acid. After filtering off with suction, there are obtained 2 g. of the fumarate of the title compound, i.e. 33% of theory; m.p. 105°-107° C.

Workup

  1. temperatureWhile cooling
  2. additionthere are now added dropwise at +10° C.
  3. customin the course of 10 minutes
  4. stirringAfter stirring overnight at ambient temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried with anhydrous sodium sulphate
  7. distillationdistilled in a vacuum
  8. dissolutionThe remaining oil is dissolved in ethanol
  9. additionconverted into the salt by the addition of 1.2 g
  10. filtrationAfter filtering off with suction, there
  11. customare obtained 2 g

Sources & evidence

ORD record
ord-a69a35933c1f46ccb610bee482dbcbcd
Source dataset
uspto-grants-1994_01
Patent number
US05280031

Reaction notes

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