2-Chlorobenzenesulfonyl chloride → 1-(2-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid ethyl ester

HRID 220205Notes

Reaction equation

HRID 220205 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3].CCN(C(C)C)C(C)C.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([S:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[Cl:22])(=[O:31])=[O:30])[CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 12896004Ethyl piperidine-3-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 38620101-(2-Chloro-benzenesulfonyl)-piperidine-3-carboxylic acid ethyl esterYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.87 g piperidine-3-carboxylic acid ethyl ester hydrochloride (commercially available) (20 mmol) in 40 mL DCM was added 10 mL of DIPEA (60 mmol). At room temperature 2.72 mL 2-chloro-benzenesulfonyl chloride (20 mmol) was added drop wise and stirred for 14 h. The mixture was diluted with 30 mL of DCM, washed with water (3×50 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain the crude product which was further purified by column chromatography on silica eluting with 10% ethyl acetate in hexane to yield 5.73 g (86.3%) of the title compound. (MH+) 332.16.

Workup

  1. washwashed with water (3×50 mL)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto obtain the crude product which
  6. customwas further purified by column chromatography on silica eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-decf172425a84e979d2d2cd63b4c8015
Source dataset
uspto-grants-2012_06
Patent number
US08202888B2

Reaction notes

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