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

HRID 915815Notes

Reaction equation

HRID 915815 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), 4.44.1 (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-a5c75e3731ae474782665501c6c73e9d
Source dataset
uspto-grants-2007_09
Patent number
US07268140B2

Reaction notes

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