N-Methylaniline → N-methyl-N-(prop-2-yn-1-yl)aniline

HRID 352044Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3]C.[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Br)C#C>CCCCCCC.CCOCC.C1(C)C=CC=CC=1>[CH3:6][N:7]([CH2:3][C:2]#[CH:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -10 °C

Procedure

34 ml of a 2.7M solution of n-butyllithium in n-heptane are added dropwise at room temperature under nitrogen in the course of 1 hour to a solution of 10 g (93 mmol) of N-methylaniline in 100 ml of absolute ether. The temperature increases to reflux of the reaction mass. After 1 hour's reflux, the yellow solution is cooled to −10° C. and then in the course of 30 minutes a solution of 11.3 g (102 mmol) of propargyl bromide in toluene is added dropwise. The mixture is then stirred at room temperature for 8 hours. After customary aqueous working-up, the product of formula (101a) is purified by distillation. A yellow oil is obtained.

Workup

temperatureThe temperature increases
temperatureto reflux of the reaction mass
temperatureAfter 1 hour's reflux
distillationAfter customary aqueous working-up, the product of formula (101a) is purified by distillation
customA yellow oil is obtained

Sources & evidence

ORD record: ord-f75078f2d71a4ab2a1dbbdcd936008e3
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743940B2

Reaction notes

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