Iodine → 1-Butyl-4-(3-(dodecyloxy)-3-oxopropyl)-1-methylpiperazin-1-ium bromide

HRID 2191197Notes

Reaction equation

HRID 2191197 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:11])[CH2:4][CH2:3]1.[CH2:25]([Br:29])[CH2:26][CH2:27][CH3:28].C(O)(C)C.II>CO.C1(C)C=CC=CC=1>[Br-:29].[CH2:25]([N+:2]1([CH3:1])[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:11])[CH2:6][CH2:7]1)[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 807IodineHCID 3776IsopropanolHCID 8002Butyl bromideHCID 59270650Dodecyl 3-(4-methylpiperazin-1-yl)propanoate

Product 1

HCID 667047001-Butyl-4-(3-(dodecyloxy)-3-oxopropyl)-1-methylpiperazin-1-ium bromide

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

In a 100-mL round bottom flask, 5.0 g (0.015 moles) of dodecyl 3-(4-methylpiperazin-1-yl)propanoate and 7.3 g (0.044 moles) of butyl bromide are combined with 10 mL of isopropyl alcohol. This solution is heated to reflux overnight. Thin layer chromatography (TLC) was used to monitor the progress of the reaction with 1:1 methanol/toluene as a mobile phase and iodine to reveal the components on the plate. After the reaction is complete, the solvent and excess of butyl bromide are evaporated under vacuum. Finally, the resulting solid is dried under vacuum at 120° C. 1H-NMR (300 MHz, CDCl3): δ 3.92 (t, 5.9 Hz, 2H), 3.76 (m, 2H), 3.56 (m, 4H), 3.35 (s, 3H), 2.91 (m, 6H), 2.46 (t, 6.6 Hz, 2H), 1.67 (m, 2H), 1.47 (m, 2H), 1.12 (m, 24H), 0.74 (m, 6H). 13C-NMR (75 MHz, CDCl3): δ 170.98, 64.61, 59.14, 51.84, 45.88, 31.44, 31.28, 30.81, 29.18, 29.16, 29.13, 29.08, 28.87, 28.81, 28.11, 25.50, 25.43, 22.21, 21.96, 21.60, 13.66, 13.49.

Workup

  1. temperatureThis solution is heated
  2. temperatureto reflux overnight
  3. customthe solvent and excess of butyl bromide are evaporated under vacuum
  4. customFinally, the resulting solid is dried under vacuum at 120° C

Sources & evidence

ORD record
ord-e0a98524da184b9f80b78cd00443c372
Source dataset
uspto-grants-2012_12
Patent number
US08329620B2

Reaction notes

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