Trimethylamine → N,N,N-Trimethyl-2-oxo-2-(prop-2-yn-1-ylamino)ethanaminium bromide

HRID 708326Notes

Reaction equation

HRID 708326 reaction equation
[Br:1][CH2:2][C:3]([NH:5][CH2:6][C:7]#[CH:8])=[O:4].[CH3:9][N:10]([CH3:12])[CH3:11]>C(#N)C>[Br-:1].[CH3:9][N+:10]([CH3:12])([CH3:11])[CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7]#[CH:8]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 111596172-bromo-N-(prop-2-yn-1-yl)acetamide

Product 1

HCID 118379911N,N,N-Trimethyl-2-oxo-2-(prop-2-yn-1-ylamino)ethanaminium bromideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.6 g, 3.4 mmol) in acetonitrile (5 mL) was added trimethylamine (30% in MeOH, 5 mL). The mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was triturated with ether, resulting in the title compound (780 mg, 97%); LCMS: m/z=155.1 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 9.03 (t, J=5.3 Hz, 1H), 4.17 (s, 2H), 3.95 (dd, J=5.4, 2.6 Hz, 2H), 3.23 (s, 9H), 2.09 (s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was triturated with ether

Sources & evidence

ORD record
ord-8b2364f852df41e5ae0cdc996b161d10
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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