Triethylamine → 1-[(Dimethylphosphoryl)methyl]-4-[4-nitro-2-(trifluoromethyl)benzyl]piperazine

HRID 1255948Notes

Reaction equation

HRID 1255948 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([CH3:4])=[O:3].C(N(CC)CC)C.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>ClCCl>[CH3:4][P:2]([CH2:5][N:6]1[CH2:7][CH2:8][N:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=2[C:30]([F:31])([F:32])[F:33])[CH2:10][CH2:11]1)([CH3:1])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 203769071-[(Dimethylphosphoryl)methyl]piperazineHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 577751371-[(Dimethylphosphoryl)methyl]-4-[4-nitro-2-(trifluoromethyl)benzyl]piperazineYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[(dimethylphosphoryl)methyl]piperazine (3.6 mmol) was dissolved in 20 mL of anhydrous dichloromethane. Triethylamine (4.04 g, 11 eq.) was carefully added. The reaction solution temperature rose to 30° C. before cooling down to room temperature after 5 minutes. After 1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (60 weight %, 3.88 g, 7.9 mmol, 2.2 eq) was added in one portion, the reaction mixture was stirred at room temperature for 30 minutes under N2 protection. After the volatile components were evaporated, the reaction mixture was purified via column chromatography to give title compound as light yellow solid (740 mg). MS (LC/MS): 378.3 [M-]. 31P-NMR (300 MHz. CDCl3): 42.8.

Workup

  1. customrose to 30° C.
  2. customAfter the volatile components were evaporated
  3. customthe reaction mixture was purified via column chromatography

Sources & evidence

ORD record
ord-de6944c2e9214232aa6e292ab5838cb7
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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