Formaldehyde → Oxotremorine 1

HRID 462077Notes

Reaction equation

HRID 462077 reaction equation
[CH3:1][N:2]([CH2:6][C:7]#[CH:8])[C:3](=[O:5])[CH3:4].[CH2:9]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCOCC1>[CH3:1][N:2]([CH2:6][C:7]#[C:8][CH2:9][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:3](=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 29033Acetamide, N-methyl-N-[2-propynyl]-HCID 31268Pyrrolidine

Product 1

HCID 19716Oxotremorine 1

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere, a solution containing 13.0 g. (0.12 mole) of N-methyl-N-propargylacetamide, 5.8 g. of paraformaldehyde, 10.5 g. (0.15 mole) of pyrrolidine and a trace of cuprous chloride in 80 ml. of dioxane was refluxed for 5 hrs. and allowed to stand overnight. The mixture was filtered remaining oil was distilled and redistilled giving N-methyl-N-(4-pyrrolidino-2-butynyl)acetamide, boiling at 120° C. at 0.03 mm.

Workup

  1. additionUnder a nitrogen atmosphere, a solution containing 13.0 g
  2. filtrationThe mixture was filtered
  3. distillationwas distilled
  4. distillationredistilled

Sources & evidence

ORD record
ord-ed98a0d44b504502b844f3326f398ecc
Source dataset
uspto-grants-1977_12
Patent number
US04065471

Reaction notes

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