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

HRID 489205Notes

Reaction equation

HRID 489205 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-ef0dbd696e9e48f286ba198edb9b6560
Source dataset
uspto-grants-2005_12
Patent number
US06977258B2

Reaction notes

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