Formaldehyde → Tert-butyl 4-[(dimethylphosphoryl)methyl]piperazine-1-carboxylate

HRID 1527880Notes

Reaction equation

HRID 1527880 reaction equation
[CH2:1]=O.[CH3:3][PH:4](=[O:6])[CH3:5].[N:7]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.N#N>C(O)C>[CH3:3][P:4]([CH2:1][N:10]1[CH2:11][CH2:12][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:9]1)([CH3:5])=[O:6]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 947NitrogenHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178503022methylphosphonoylmethane

Product 1

HCID 68899702Tert-butyl 4-[(dimethylphosphoryl)methyl]piperazine-1-carboxylateYield 13.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Formaldehyde (0.954 g, 31.8 mmole, 1.2 eq. 37% WT in water), 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-575645402cfc4d83b76e25d1607b0406
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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