Sodium Bicarbonate → 1-(2-Fluoro-5-methylsulfonylphenyl)piperazine

HRID 1792486Notes

Reaction equation

HRID 1792486 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[NH2:12].Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.C(=O)(O)[O-].[Na+]>ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:4][C:3]=1[N:12]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 27746372-Fluoro-5-(methylsulfonyl)aniline

Product 1

HCID 220320111-(2-Fluoro-5-methylsulfonylphenyl)piperazineYield 39%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

10 mL solution of 432 mg 2-fluoro-5-methylsulfonylphenylamine (compound in Production Example 338) and 490 mg bis(2-chloroethyl)amine hydrochloride in 1,2-dichlorobenzene was stirred at 200° C. for 9 hours. The reaction mixture was neutralized by adding an aqueous saturated sodium bicarbonate solution and then extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 230 mg of the title compound (dark brown solid).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed
  4. customthe resulting crude product was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-301e0a8a384a44118b2bb5ca131ee775
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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