Ethyl bromoacetate → Ethyl 2-(3,5-dimethylpiperazin-1-yl)acetate

HRID 64071

Reaction equation

HRID 64071 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH:4]([CH3:8])[NH:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C1COCC1>[CH3:8][CH:4]1[NH:3][CH:2]([CH3:1])[CH2:7][N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 660562,6-Dimethylpiperazine

Product 1

HCID 63873524Ethyl 2-(3,5-dimethylpiperazin-1-yl)acetateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dimethylpiperazine (500 mg, 4.378 mmol, 1.0 eq) in THF were added K2CO3 (1.2 g, 8.75 mmol, 2.2 eq.) and ethyl 2-bromoacetate (731 mg, 4.378 mmol, 1 eq). The mixture was stirred at RT for 4 h and then quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 34% yield (0.3 g). LC-MS (ESI): Calculated mass: 200.0; Observed mass: 201.0 [M+H]+ (rt: 0.102 min).

Workup

  1. customquenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 34% yield (0.3 g)
  5. custom201.0 [M+H]+ (rt: 0.102 min)

Sources & evidence

ORD record
ord-b40f9fa7dd3a44feb2f65f95e77c5fde
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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