Nitrogen mustard hydrochloride → 1-(4-Methylpiperazin-1-yl)naphthalen-2-ol

HRID 481358

Reaction equation

HRID 481358 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13].Cl.Cl[CH2:16][CH2:17][N:18]([CH2:20][CH2:21]Cl)[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[CH3:19][N:18]1[CH2:20][CH2:21][N:2]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[OH:13])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 5184691-Amino-2-naphthol hydrochloride

Product 1

HCID 190661661-(4-Methylpiperazin-1-yl)naphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-Aminonaphthalen-2-ol hydrochloride (5 g, 25.6 mmol) is brought to the reflux point of 1-butanol (100 ml) in the presence of 2-chloro-N-(chloroethyl)-N-methylethanamine hydrochloride (4.9 g, 25.6 mmol) and sodium carbonate (5.4 g, 51 mmol). After 48 h, the reaction mixture is concentrated and impregnated onto silica and then purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia

Sources & evidence

ORD record
ord-852d70383fab463598ddab0596238037
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Linked notes

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