2-Aminophenol → o-(1-Piperazinyl)phenol

HRID 481363Notes

Reaction equation

HRID 481363 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[Na+].[Na+].Cl.C[N:17]([CH2:21][CH2:22]Cl)[CH2:18][CH2:19]Cl>C(O)CCC>[N:1]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH2:22][CH2:21][NH:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium Carbonate

Product 1

HCID 70530o-(1-Piperazinyl)phenol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
123 °C

Procedure

2-Aminophenol (6 g; 54 mmol) is dissolved in 1-butanol (110 ml) in the presence of sodium carbonate (2.9 g; 27.5 mmol) and N-methylbis(2-chloroethyl)amine hydrochloride (11.1 g; 58 mmol). The suspension is heated at 123° C. for 3 days. The butanol is evaporated off under reduced pressure and compound 43A is purified by flash chromatography with the following mixtures of eluents: NH4 OH/acetone/CH2Cl2 (0.5/20/80) and then NH4 OH/methanol/CH2Cl2 (1/5/95).

Workup

  1. customThe butanol is evaporated off under reduced pressure and compound 43A
  2. customis purified by flash chromatography with the following mixtures of eluents

Sources & evidence

ORD record
ord-76dea39994dd46e599c409f42727a191
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Reaction notes

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