Formaldehyde → HCID 68462714, compound

HRID 506892Notes

Reaction equation

HRID 506892 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([OH:16])[C:14]#[CH:15].C=O.O.[CH:20](Cl)(Cl)[Cl:21]>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[ClH:21].[ClH:21].[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:20][C:15]#[C:14][CH2:13][OH:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 6212ChloroformHCID 70961-PhenylpiperazineHCID 7859Propargyl alcohol

Product 1

HCID 68462714HCID 68462714, compound

Reagents, catalysts & solvents 1

HCID 165397Cupric acetate monohydrateCatalyst

Procedure

1-Phenylpiperazine (16.2 g; 0.10 mole) is weighed to propargyl alcohol (11.8 ml; 0.20 mole), copper(II) acetate monohydrate (1.0 g; 5.2 mmoles) is added to it, and 37% aqueous formaline (50 ml) is pipetted to the reaction mixture under stirring. The green suspension is refluxed for 2 hours. Then it is cooled, water and chloroform are added to it and the pale green substance insoluble in both phases are filtered off. The aqueous phase is extracted twice with chloroform, the combined organic phases are dried over sodium sulfate and evaporated. The residual brown oil is dissolved in ethyl acetate, and a solution of 2 molar equivalents of hydrogen chloride in ethyl acetate is dropped to it under stirring. The separated white salt is filtered off, digested while hot with isopropanol, cooled and filtered.

Workup

  1. temperatureThe green suspension is refluxed for 2 hours
  2. temperatureThen it is cooled
  3. filtrationthe pale green substance insoluble in both phases are filtered off
  4. extractionThe aqueous phase is extracted twice with chloroform
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. customevaporated
  7. dissolutionThe residual brown oil is dissolved in ethyl acetate
  8. additiona solution of 2 molar equivalents of hydrogen chloride in ethyl acetate is dropped to it
  9. stirringunder stirring
  10. filtrationThe separated white salt is filtered off
  11. temperaturecooled
  12. filtrationfiltered

Sources & evidence

ORD record
ord-188be9ebceb94f32bdc900cdfa782155
Source dataset
uspto-grants-2010_08
Patent number
US07786129B2

Reaction notes

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