2-Chlorobenzenesulfonyl chloride → 1-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2193995Notes

Reaction equation

HRID 2193995 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:7][CH2:8][N:9]([S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])(=[O:25])=[O:24])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 667876761-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl esterYield 49.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.5 g) was dissolved in pyridine (20 ml) at RT and 2-chlorobenzenesulfonylchloride (0.49 g) was added and the mixture was stirred overnight at RT. The pyridine was evaporated off, the residue then dissolved in AcOEt and washed with 0.05M HCl and brine. The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 25%) to give the desired 1-(2-chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.448 g) as light brown oil. MS (ESI): 390.11 (MH+).

Workup

  1. customThe pyridine was evaporated off
  2. dissolutionthe residue then dissolved in AcOEt
  3. washwashed with 0.05M HCl and brine
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 25%)

Sources & evidence

ORD record
ord-d831349fccd744439d9bb8c6b0cc1230
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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