Propargyl bromide → HCID 129865535, compound

HRID 879032Notes

Reaction equation

HRID 879032 reaction equation
[CH2:1]([Br:4])[C:2]#[CH:3].[CH3:5][N:6]([CH3:10])[CH2:7][CH2:8][OH:9].[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1>>[CH2:1]([O:9][CH2:8][CH2:7][N+:6]([CH3:11])([CH3:10])[CH3:5])[C:2]#[CH:3].[Br-:4].[CH2:13]([O:14][CH2:15][CH2:11][N+:6]([CH3:10])([CH3:7])[CH3:5])[C:12]#[CH:1]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 79022-(Dimethylamino)ethanolHCID 8028Tetrahydrofuran

Product 2

HCID 76850140HCID 76850140, compoundHCID 129865535HCID 129865535, compoundYield 84%

Procedure

Propargyl-choline was synthesized by the following procedure: 4 grams of propargyl bromide (80% solution in toluene, 34 mmoles) were slowly added to 3 grams of dimethyl-ethanolamine (34 mmoles) in 10 mL of dry THF, while stirring on ice. The mix was allowed to reach room temperature and stirring was continued overnight. The resulting white solid was filtered and washed extensively with cold THF (10 times, 20 mL), to afford pure propargyl-choline bromide (5.9 grams, 84% yield) as a white solid. Propargyl-choline: white crystals, molecular weight: 128.19, ES-API LC/MS: [M]+=128.1, 1H NMR (600 MHz, CD3OD): 4.78 (1H, b), 4.49 (2H, d, J=2.4 Hz), 4.03 (2H, t, J=4.5 Hz), 3.64 (2H, m), 3.30 (6H, s), 13C NMR (600 MHz, CD3OD): δ3.2 (CH, d, J=101.4 Hz), 72.7 (C, d, J=21.0 Hz), 66.4 (CH2, t, J=60.3 Hz), 56.7 (CH2, t, J=47.4 Hz), 56.5 (CH2, t, J=45.9 Hz), 52.2 (C2H6, q, J=31.2 Hz), 49.05 (CD3OD).

Workup

  1. customto reach room temperature
  2. stirringstirring
  3. filtrationThe resulting white solid was filtered
  4. washwashed extensively with cold THF (10 times, 20 mL)

Sources & evidence

ORD record
ord-fdab535876224127b05bf7f0342f856b
Source dataset
uspto-grants-2015_03
Patent number
US08987514B2

Reaction notes

Loading…