Ethyl bromoacetate → 1-Piperazineacetic acid, 4-methyl-, ethyl ester

HRID 64060Notes

Reaction equation

HRID 64060 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 2069391-Piperazineacetic acid, 4-methyl-, ethyl esterYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methylpiperazine (1 g, 8.771 mmol, 1.0 eq) in DMF were added K2CO3 (265 m g, 21.927 mmol, 2.5 eq) and ethyl 2-bromoacetate (167 mg, 13.15 mmol, 1.5 eq). The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 76.4% yield. (1.3 g).

Workup

  1. customquenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 76.4% yield

Sources & evidence

ORD record
ord-d5fa8216baf24c95ae21cbdbec2565c0
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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