4-Chlorobenzylpiperazine → 1-(((4-Chlorobenzyl)amino)carbonyl)-4-(4-chlorobenzyl)piperazine

HRID 1861854Notes

Reaction equation

HRID 1861854 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:25]=[CH:24][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][C:16]3[CH:24]=[CH:25][C:13]([Cl:12])=[CH:14][CH:15]=3)[CH2:23][CH2:22]2)=[O:9])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 1348264-ChlorobenzylpiperazineHCID 33723791-Chloro-4-(isocyanatomethyl)benzene

Product 1

HCID 222649801-(((4-Chlorobenzyl)amino)carbonyl)-4-(4-chlorobenzyl)piperazineYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chlorobenzylisocyanate (0.59 g, 3.5 mmol) in anhydrous THF (15 mL) at 0° C. was added 1-(4-chlorobenzyl)piperazine (0.74 g, 3.5 mmol). The resultant mixture was stirred at ambient temperature. After 20 hours the mixture was concentrated of volatiles. The resulting solid was washed with ethyl acetate and dried in vacuo to afford 0.72 g of 1-(((4-chlorobenzyl)amino)carbonyl)-4-(4-chlorobenzyl)piperazine as a white solid; NMR (CDCl3) 7.4 (m, 4), 7.3 (m, 2), 7.2 (m, 2), 4.4-4.1 (m, 6), 3.6 (m, 4), 3.0 (m, 2) ppm.

Workup

  1. concentrationAfter 20 hours the mixture was concentrated of volatiles
  2. washThe resulting solid was washed with ethyl acetate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e7a4de812865445ea99a6f493ca735fc
Source dataset
uspto-grants-2003_03
Patent number
US06534509B1

Reaction notes

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