Nitrogen mustard hydrochloride → 1-(2-Bromo-5-nitrophenyl)-4-methylpiperazine

HRID 1708387Notes

Reaction equation

HRID 1708387 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].Cl.Cl[CH2:14][CH2:15][N:16]([CH2:18][CH2:19]Cl)[CH3:17]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:19][CH2:18][N:16]([CH3:17])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 5935Nitrogen mustard hydrochlorideHCID 826072-Bromo-5-nitroaniline

Product 1

HCID 224145891-(2-Bromo-5-nitrophenyl)-4-methylpiperazineYield 26.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A suspension of 2-bromo-5-nitrobenzenamine (26.0 g) and 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (23.0 g) in chlorobenzene (150 ml) was treated according to the method of Intermediate 56. Purification by FCC eluting with System A (300:8:1 gradient to 200:8:1) gave the title compound as a brown solid (9.498 g) m.p. 100°-103° C.

Workup

  1. additionwas treated
  2. customPurification by FCC
  3. washeluting with System A (300:8:1 gradient to 200:8:1)

Sources & evidence

ORD record
ord-12a072e796484ceaaf8c4e13ea56113e
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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