Formaldehyde → Succinimide, N-(4-(1-pyrrolidinyl)-2-butynyl)-

HRID 462078Notes

Reaction equation

HRID 462078 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])[C:2]#[CH:3].[CH2:11]=O.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>O1CCOCC1>[N:13]1([CH2:11][C:3]#[C:2][CH2:1][N:4]2[C:8](=[O:9])[CH2:7][CH2:6][C:5]2=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 4737238SBB039933

Product 1

HCID 199231Succinimide, N-(4-(1-pyrrolidinyl)-2-butynyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the example given in Example 1B, 19.1 g. (0.15 mole) of N-propargylsuccinimide was caused to react with 6.3 g. of paraformaldehyde and 14.2 g. (0.2 mole) of pyrrolidine in 100 ml. of dioxane in the presence of a trace of cuprous chloride. The reaction was refluxed for 5 hrs. and allowed to stand overnight. After filtration of the reaction mixture and removal of the solvent from the filtrate, the residual oil was distilled to give N-[4-(1-pyrrolidinyl)-2-butynyl]-succinimide boiling at 155° C. at 0.04 mm. This product solidified, and after recrystallization from ether, melted at 93.0 to 94.0° C. (corr.).

Workup

  1. customto react with 6.3 g
  2. temperatureThe reaction was refluxed for 5 hrs
  3. filtrationAfter filtration of the reaction mixture and removal of the solvent from the filtrate
  4. distillationthe residual oil was distilled

Sources & evidence

ORD record
ord-bd34ff7e6b61446f962aeec4fd12bb04
Source dataset
uspto-grants-1977_12
Patent number
US04065471

Reaction notes

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