Triethylamine → HCID 22242886, compound

HRID 891737Notes

Reaction equation

HRID 891737 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([CH2:21][O:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15].C(N(CC)CC)C.C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:23]([O:22][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=2)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 782054-Nitrobenzyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22242886HCID 22242886, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(t-butoxycarbonyl)piperazine (1.50 g, 8.05 mmol) in methylene chloride (68 ml) were added chloroformic acid p-nitrobenzyl ester (1.90 g, 8.86 mmol) and triethylamine (1.24 ml, 8.86 mmol) in an ice bath. The mixture was stirred in the ice bath for 1.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The obtained organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate=(1:3) as the eluant to afford 1-(t-butoxycarbonyl)-4-(p-nitrobenzyloxycarbonyl)piperazine (2.60 g, yield 89%) as a pale yellow oil.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe obtained organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f5dc8f9c6ff2467cb8802fcd4efb0207
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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