Methyl bromoacetate → benzyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 518714Notes

Reaction equation

HRID 518714 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20]>C1COCC1>[CH3:22][O:21][C:19](=[O:20])[CH2:18][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 66728950benzyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of benzyl piperazine-1-carboxylate (0.5 g, 2.270 mmol) and TEA (0.949 mL, 6.81 mmol) in THF (10 mL) was added methyl 2-bromoacetate (0.230 mL, 2.497 mmol) dropwise. The reaction was stirred at 65° C. After 1 hour, the reaction mixture was concentrated, and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to generate benzyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate as a clear oil (0.61 g, 92% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-767db109e6f4462cbca2356375895b2b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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