1-Ethylpiperazine → 1-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine

HRID 1051258Notes

Reaction equation

HRID 1051258 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[CH2:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:17].CCN(C(C)C)C(C)C>ClCCl>[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:20][CH2:19]1)[CH3:17]

Participants

5

Reactant 3

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 576852631-Ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazineYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (34 g, 120 mmol) obtained in Step (1) above was stirred in a solvent of dichloromethane (300 mL). The reaction solution was added with 1-ethylpiperazine (15.97 mL, 126 mmol) and DIPEA (27.2 mL, 156 mmol), followed by stirring for about 3 hours at room temperature. The reaction mixture was diluted with dichloromethane, washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (21.7 g, 57%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-226199639dab4f8f9c463ecd71fa16c3
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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