Ethyl bromoacetate → HCID 86687051, compound

HRID 2282469Notes

Reaction equation

HRID 2282469 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH:5]1[CH2:10][OH:11].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:7]1[CH2:8][CH2:9][N:4]([CH3:3])[CH:5]([CH2:10][OH:11])[CH2:6]1)[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 574815822-Piperazinemethanol, 1-methyl-, hydrochloride (1:2)

Product 1

HCID 86687051HCID 86687051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (1-methyl-2-piperazinyl)methanol dihydrochloride (500 mg, 2.46 mmol), ethyl bromoacetate (410 mg, 2.46 mmol), K2CO3 (1.02 g, 7.38 mmol) and MeCN (15 mL) were heated to reflux for 18 h. After cooling, the mixture was filtered and concentrated in vacuo. The title compound was isolated as a colourless oil (525 mg, 98%) and used without further purification. 1H NMR (300 MHz, CDCl3): 1.25 (3H, t, J 7.0), 2.35 (3H, s), 2.35-2.59 (4H, m), 2.76-2.90 (3H, m), 3.19 (2H, m), 3.44 (1H, dd, J 11.3, 2.0), 3.87 (1H, dd, J 11.3, 4.0), 4.15 (2H, q, J 7.1).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 18 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b33286c683943519924e078cace0259
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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