Triethylamine → HCID 22400684, compound

HRID 863817Notes

Reaction equation

HRID 863817 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].C(N([CH2:19][CH3:20])CC)C.C([O:23][P:24](Cl)(OCC)=O)C.[CH2:30]1[CH2:34]OCC1.O>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([P:24]([CH2:19][CH3:20])([CH2:34][CH3:30])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 22400684HCID 22400684, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

N-tert-butyloxycarbonylpiperazine (1.0 g, 5.34 mmol) was dissolved in 5 mL of THF: water (1:1) and cooled in an ice bath. Triethylamine (1.45 mL, 10.68 mmol), followed by diethylchlorophosphate (1.16 mL, 8.01 mmol) in 5 mL of ether were added, and stirred at 0° C. for 1 hour and at room temperature for 2 hours. Solvents were removed and 40 mL of ethyl acetate was added to the residue. The ethyl acetate layer was washed with brine (30 mL×3) and dried over anhydrous sodium surf ate. After filtered, the filtrate was concentrated in vacuo to yield 1.5 g of N-tert-butyloxycarbonyl--N'-diethylphosphoryl-piperazine in 88% yield as an oil. MS m/z M+H=323, M+NH4 =340. H1 -NMR (in CDCl3) δ=1.32 (t, 6H, 2×CH3), 1.48 (s, 9H, Boc), 3.1 (m, 4H, piperazine), 3.37 (t, 4H, piperazine), 4.05 (m, 4H, 2×OCH2). The obtained N-tert-butyloxycarbonyl--N'-diethylphosphoryl-piperazine (1.5 g, 4.66 mmol) was dissolved in I 0 mL of 10% trifluoroacetic acid in methylene chloride and stirred at room temperature for 30 minutes. Solvent and trifluoroacetic acid were removed to obtain 1.6 g of N-diethylphosphorylpiperazine trifluoroacetic acid salt in quantitative yield. MS m/z M+H=223, H1 -NMR (in MeOH-d4) δ=1.35 (m, 6H, 2×CH3), 3.19 (m, 4H, piperazine), 3.37 (m, 4H, piperazine), 4.05 (m, 4H, 2×OCH2).

Workup

  1. temperaturecooled in an ice bath
  2. additionwere added
  3. customSolvents were removed
  4. addition40 mL of ethyl acetate was added to the residue
  5. washThe ethyl acetate layer was washed with brine (30 mL×3)
  6. dry with materialdried over anhydrous sodium surf
  7. filtrationAfter filtered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-51ee48027b274ccf903fab6d0c1aebae
Source dataset
uspto-grants-1996_10
Patent number
US05561140

Reaction notes

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