Acetone → 1-[2-(Acetylsulfanyl)ethyl]-1,4-dimethylpiperazin-1-ium bromide

HRID 485228

Reaction equation

HRID 485228 reaction equation
[S:1]1[CH:5]=[CH:4]C=[C:2]1[CH2:6]C(OCC[Br:12])=O.[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.CC(C)=[O:23]>>[Br-:12].[C:2]([S:1][CH2:5][CH2:4][N+:14]1([CH3:13])[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)(=[O:23])[CH3:6]

Participants

4

Reactant 3

HCID 180AcetoneHCID 78181,4-DimethylpiperazineHCID 570913592-Bromoethyl thiolacetate

Product 1

HCID 202033661-[2-(Acetylsulfanyl)ethyl]-1,4-dimethylpiperazin-1-ium bromide

Conditions

Temperature
25 °C

Procedure

A solution of 2-bromoethyl thiolacetate *(2.20 g, 0.012 mol) and 1,4-dimethylpiperazine (1.95 mL, 0.014 mol) in acetone (4 mL) was stirred at 50° C. for 65 h. After cooling to 25° C., the liquid phase was decanted from the gum which was triturated twice in diethyl ether; a hygroscopic yellowish powder, 3.2 g (90%) was obtained; ir (Nujol) νmax : 1685 (C=O of thioester) cm-1 ; 1Hmr (D2O) δ: 2.37, 2.39 ##STR122##

Workup

  1. customthe liquid phase was decanted from the gum which
  2. customwas triturated twice in diethyl ether
  3. customa hygroscopic yellowish powder, 3.2 g (90%) was obtained

Sources & evidence

ORD record
ord-71534d3bdf0f4eb3a161bb0157aa94b6
Source dataset
uspto-grants-1985_08
Patent number
US04536335

Linked notes

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