Nitrogen mustard hydrochloride → 3-(4-Methylpiperazin-1-yl)phenol

HRID 481348Notes

Reaction equation

HRID 481348 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:11][CH2:12][N:13]([CH2:15][CH2:16]Cl)[CH3:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:14][N:13]1[CH2:15][CH2:16][N:1]([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 115683-Aminophenol

Product 1

HCID 110114553-(4-Methylpiperazin-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3-Aminophenol (2 g, 18 mmol) is brought to the reflux point of 1-butanol (30 ml) in the presence of 2-chloro-N-(chloroethyl)-N-methylethanamine hydrochloride (3.5 g, 18 mmol) and sodium carbonate (95 mg, 9 mmol). After 48 h, the reaction mixture is concentrated and adsorbed on silica and then purified by flash chromatography with a mixture (90/10) of dichloromethane/methanol.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by flash chromatography with a mixture (90/10) of dichloromethane/methanol

Sources & evidence

ORD record
ord-ffb750504ba040e3b955ab2a60a78e90
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Reaction notes

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