Triethylamine → 2-Bromo-1-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-ethanone

HRID 220837Notes

Reaction equation

HRID 220837 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].Cl.[CH3:7][C:8]([CH3:18])([CH3:17])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl>[Br:1][CH2:2][C:3]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[CH3:7])[CH2:12][CH2:13]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 231123491-(3,3-Dimethyl-butyl)-piperazine hydrochloride

Product 1

HCID 575551982-Bromo-1-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-ethanoneYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetyl bromide (0.52 ml, 6.0 mmol) was added to a solution of 1-(3,3-dimethyl-butyl)-piperazine hydro-chloride from Example E4 (1.5 g, 5.7 mmol) in dichloromethane (20 ml) and triethylamine (3.57 ml, 25.6 mmol) at 0° C. The mixture was stirred for 20 h at room temperature, washed with saturated NaHCO3, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane) to yield the title compound (220 mg, 13%).

Workup

  1. washwashed with saturated NaHCO3
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane)

Sources & evidence

ORD record
ord-37e75c21599e4b2e950db85bc8e52cbd
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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