Potassium Carbonate → Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

HRID 397693Notes

Reaction equation

HRID 397693 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6]Br)[CH3:2].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6][N:19]1[CH2:18][CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:21][CH2:20]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 23000690Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl-3-bromoproprionate (1.67 ml) was added to a suspension of tert-butyl-1-piperazine carboxylate (2.43 g) and potassium carbonate (2.16 g) in acetonitrile (30 ml). The reaction mixture was stirred for 56 hrs at room temperature, after which time the solvent was removed under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford tert-butyl 4-(3-ethoxy-3-oxopropyl)-1-piperazinecarboxylate (2.44 g) as an oil.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0608739503a34c73b49ff52851d65f54
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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