Propargyl bromide → N-(2,2-Dimethoxyethyl)prop-2-yn-1-amine

HRID 1763776Notes

Reaction equation

HRID 1763776 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(N(CC)CC)C.Br[CH2:16][C:17]#[CH:18]>C1C=CC=CC=1>[CH2:18]([NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])[C:17]#[CH:16]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 20307436N-(2,2-Dimethoxyethyl)prop-2-yn-1-amine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2,2-Dimethoxyethyl)amine (23 grams), triethylamine (31 ml) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. 1-Bromo-2-propyne (16.5 grams) was added dropwise with stirring to the reaction mixture at room temperature. After the addition was completed stirring was continued for a period of about 1 hour. After this time the reaction mixture was filtered and stripped of solvent. The residue was then distilled to yield the desired product N-propargyl-N-(2,2-dimethoxyethyl)amine having a boiling point of 70° C. at 1 mm of Hg pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition
  3. stirringwas completed stirring
  4. filtrationAfter this time the reaction mixture was filtered
  5. distillationThe residue was then distilled

Sources & evidence

ORD record
ord-aa97379b6455429a9aaa962c31176061
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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