Formaldehyde → 1-[4-(Diethylamino)-2-butynyl]pyrrolidine

HRID 462083Notes

Reaction equation

HRID 462083 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][C:5]#[CH:6])[CH3:2].[CH2:9]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>O1CCOCC1>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][C:5]#[C:6][CH2:9][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 20010DietylaminopropinHCID 31268Pyrrolidine

Product 1

HCID 213904851-[4-(Diethylamino)-2-butynyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the procedure given in Example 1B, 7.8 g. (0.07 mole) of diethylpropargylamine, 3.8 g. of paraformaldehyde, 5.7 g. (0.08 mole) of pyrrolidine, and a trace of cuprous chloride in 80 ml. of dioxane was refluxed for 4 hours and allowed to stand overnight. After distillation and redistillation, the product, 1-[4-(diethylamino)-2-butynyl]pyrrolidine was obtained as a clear oil boiling at 68.0° C. at 0.05 mm.; ND25 = 1.4770.

Workup

  1. distillationAfter distillation and redistillation

Sources & evidence

ORD record
ord-923b6beafcf340ab9f38adcede1c9ede
Source dataset
uspto-grants-1977_12
Patent number
US04065471

Reaction notes

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