Ethanol → HCID 68912066, compound

HRID 1255946Notes

Reaction equation

HRID 1255946 reaction equation
[CH3:1][PH:2](=[O:4])[CH3:3].[N:5]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.N#N.[CH2:20](O)C>>[CH2:11]=[O:12].[CH3:1][P:2]([CH2:20][N:8]1[CH2:9][CH2:10][N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:7]1)([CH3:3])=[O:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 947NitrogenHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178503022methylphosphonoylmethane

Product 1

HCID 68912066HCID 68912066, compound

Conditions

Temperature
90 °C

Procedure

Dimethylphosphane oxide (2.25 g, 28.8 mmole, 1.09 eq.) and tert-butyl piperazine-1-carboxylate (14.93 g, 26.5 mmole, 1.0 eq.) were dissolved in 20 mL of anhydrous ethyl alcohol. The reaction mixture was sealed in a seal-tube with N2 atmosphere and stirred at 90 Celsius overnight. The reaction mixture was then cooled to room temperature and rotaevaporate to remove volatile components. The light yellow thick oil obtained was purified via column chromatography (elution sequence: 100% hexane—10% EtOAc/hexane—100% EtOAc—10% MeOH/EtOAc/sat.NH3) to yield 1.01 g of the desired compound as white solid. MS (LC/MS): 299.2 [M+Na]

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customto remove volatile components
  3. customThe light yellow thick oil obtained
  4. customwas purified via column chromatography (elution sequence: 100% hexane—10% EtOAc/hexane—100% EtOAc—10% MeOH/EtOAc/sat.NH3)

Sources & evidence

ORD record
ord-0cf29b56292947a38d03bcbdd17c87df
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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