Hydrochloric Acid → 4-Chloro-2-{[(4-fluorophenyl)sulfonyl]methyl}-6-(4-methylpiperazin-1-yl)aniline

HRID 227302Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:5]([N+:15]([O-])=O)=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1.Cl.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)[C:5]([NH2:15])=[C:4]([CH2:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:20])=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1-{5-chloro-2-nitro-3-{[(4-fluorophenyl)sulfonyl]methyl}phenyl}-4-methylpiperazine (1.0 mmol) in methanol is treated with Sn foil (593.3 mg), followed by 5.8 mL of 12 M HCl, heated at 60° C. for 4 h (until reaction is complete by thin layer chromatography), cooled to 0° C., treated with solid NaOH to pH>10 and extracted with CH2Cl2. The extracts are combined, washed with water and concentrated to dryness in vacuo to give the title compound.

Workup

custom(until reaction is complete by thin layer chromatography)
temperaturecooled to 0° C.
extractionextracted with CH2Cl2
washwashed with water
concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record: ord-0214e0c5e3fa45bf8f1b4d4143c2295b
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560470B2

Reaction notes

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