Piperidine → Bromo-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester

HRID 1889170Notes

Reaction equation

HRID 1889170 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([Br:16])[C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([Br:16])[C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59610030Bromo-(4-chlorosulfonyl-phenyl)-acetic acid ethyl ester

Product 1

HCID 59610039Bromo-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl esterYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Bromo-(4-chlorosulfonyl-phenyl)-acetic acid ethyl ester (2.08 gm, 6.38 mmol) was taken in DCM (63 ml) under argon atmosphere and cooled to 0-5° C., piperidine (0.56 ml, 5.74 mmol) was added dropwise to the mixture at 0-5° C. Reaction mixture was then stirred at room temperature for 30 min. Reaction mixture was washed with water followed by brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product, which was purified by flash column chromatography over silica gel using 30-50% ethyl acetate in hexane as eluent to give bromo-[4-(piperidine-1-sulfonyl)-phenyl]-acetic acid ethyl ester (1.2 gm).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by flash column chromatography over silica gel using 30-50% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-e585ae54d88d46c6b6b7e50c8f1f531d
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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