Pyridine → N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamide

HRID 858578Notes

Reaction equation

HRID 858578 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:12]([CH3:11])(=[O:14])=[O:13])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 28560458N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.5 g, 2.49 mmol), in anhydrous CH2Cl2 (5 mL) under argon were added methane sulfonyl chloride (0.23 mL, 2.99 mmol) and Pyridine (0.30 mL, 3.73 mmol). The resulting solution was stirred at 25° C. for 3 hrs. The reaction mixture was quenched with 1 N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (80% EtOAc in hexanes) to give the product (0.40 g, 58%) as a white solid.

Workup

  1. customThe reaction mixture was quenched with 1 N HCl
  2. extractionextracted with EtOAc (30 mL)
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-efb1bf49ff7544b984f4837cf26f0507
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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