Hydrochloric Acid → tert-Butyl 4-acryloylpiperazine-1-carboxylate

HRID 2279680Notes

Reaction equation

HRID 2279680 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.Cl>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 58593060tert-Butyl 4-acryloylpiperazine-1-carboxylateYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloylchlorid (0.8 ml, 9.8 mmol, 1 eq) was added dropwise to a stirred ice-cold solution of piperazine 1-carboxylic acid tert butyl ester (2 g, 9.8 mmol, 1 eq) and triethylamine (1.4 ml, 9.8 mmol, 1 eq) in dichloromethane (50 mL) at 0° C. The mixture was then stirred and allowed to come to room temperature over 2 hours. 1M Hydrochloric acid solution (50 mL) was added to the mixture, and the two layers were separated. The organic phase was washed with saturated sodium hydrogen carbonate solution (2×50 ml) and saturated sodium chloride solution (50 ml) and dried over MgSO4. After filtration, the solvent is evaporated. The residue was purified by chromatography (ethyl acetate/n-hexane 1/1) to give the product (1.26 g, 49%) as a white solid.

Workup

  1. customthe two layers were separated
  2. washThe organic phase was washed with saturated sodium hydrogen carbonate solution (2×50 ml) and saturated sodium chloride solution (50 ml)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. customthe solvent is evaporated
  6. customThe residue was purified by chromatography (ethyl acetate/n-hexane 1/1)

Sources & evidence

ORD record
ord-83e43deb40654c0496912495c0e4081b
Source dataset
uspto-grants-2015_09
Patent number
US09133213B2

Reaction notes

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