3-Chloro-2-methylaniline → 1-(3-Chloro-2-methylphenyl)piperazine hydrochloride

HRID 2185468Notes

Reaction equation

HRID 2185468 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]Cl>ClC1C=CC=CC=1>[ClH:9].[Cl:9][C:6]1[C:7]([CH3:8])=[C:2]([N:1]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 224584741-(3-Chloro-2-methylphenyl)piperazine hydrochlorideYield 176.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 6-amino-2-chlorotoluene (158.66 g) and bis-(2-chloroethyl)amine hydrochloride (200.0 g) in chlorobenzene (800 mL) was allowed to reflux for 3 days. After cooling, the reaction mixture was filtered and then washed with ether to give the titled compound (244.3 g) as a white powder: 1H NMR (400 MHz, DMSO-d6) δ 2.29 (s, 3H), 3.06 (m, 4H), 3.22 (m, 4H), 7.05 (dd, J=2.0, 6.8 Hz, 1H), 7.17-7.23 (m, 2H), and 9.40 (br s, 2H).

Workup

  1. temperatureto reflux for 3 days
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-04bf5ebc73bc4c2c99e51a4bc15f46e0
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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