Trifluoroacetic acid → 1-[(Dimethylphosphoryl)methyl]piperazine

HRID 1255947Notes

Reaction equation

HRID 1255947 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)([CH3:4])=[O:3].C(O)(C(F)(F)F)=O>ClCCl>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68899702Tert-butyl 4-[(dimethylphosphoryl)methyl]piperazine-1-carboxylate

Product 1

HCID 203769071-[(Dimethylphosphoryl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-butyl 4-[(dimethylphosphoryl)methyl]piperazine-1-carboxylate (1.01 g, 3.66 mmole) was dissolved in 7 mL of anhydrous dichloromethane. At 0° C., 7 mL of TFA:DCM=1:1 solution was added in 3 portions. The reaction mixture was stirred at this temperature for 15 minutes before another 3.5 mL of TFA was added, and then continued to stir at room temperature for 2 hours. Volatile components were evaporated and yield light yellow oil. The crude mixture was directly carried into next step. MS (LC/MS): 199.2 [M+Na]

Workup

  1. additionwas added
  2. customVolatile components were evaporated
  3. customyield light yellow oil

Sources & evidence

ORD record
ord-2d3641e6da5a411b89d357f8357b0906
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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