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

HRID 1292990Notes

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-60f79a76e9a14d5fa2873efca8b4ba2d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238696B2

Reaction notes

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