Potassium Carbonate → 1,3-Dimethyl 2-(4-((tert-butoxy)carbonyl)piperazin-1-yl)propanedioate

HRID 2202161Notes

Reaction equation

HRID 2202161 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10].[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(#N)C>[C:26]([O:25][C:23]([N:17]1[CH2:22][CH2:21][N:20]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])[CH2:19][CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70087Dimethyl bromomalonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 578486921,3-Dimethyl 2-(4-((tert-butoxy)carbonyl)piperazin-1-yl)propanedioateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.5 g (141 mmol) of potassium carbonate and then 19.5 ml (134 mmol) of dimethyl bromomalonate are added to a solution of 25 g (134 mmol) of tert-butyl piperazine-1-carboxylate in 300 ml of acetonitrile. The reaction medium is stirred at ambient temperature for 24 h and then filtered in order to remove the insoluble salts, and concentrated under vacuum. The crude residue obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 41 g (97%) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)malonate are obtained in the form of a light oil.

Workup

  1. filtrationfiltered in order
  2. customto remove the insoluble salts
  3. concentrationconcentrated under vacuum
  4. customThe crude residue obtained
  5. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-d3cb43a60cf74e229ae1aa74a6a62d60
Source dataset
uspto-grants-2016_06
Patent number
US09365529B2

Reaction notes

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