Benzenesulfonyl chloride → HCID 66787540, compound

HRID 2381169Notes

Reaction equation

HRID 2381169 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH2:7][CH2:8][N:9]([S:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:25])=[O:24])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 66787314HCID 66787314, compound

Product 1

HCID 66787540HCID 66787540, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(3-Methoxy-propyl)-piperidine-4-carboxylic acid ethyl ester (3.36 g) was dissolved under an argon atmosphere in pyridine (80 ml), benzensulfonyl chloride (2.59 g) was added and the mixture was stirred overnight at RT. The pyridine was evaporated off, the residue dissolved in ethyl acetate and washed with 0,05M HCl and brine. The layers were separated, the organic layer was dried over sodium sulphate, the solvent was then removed in vacuo and the crude oil was purified by flash chromatography over silica gel (AcOEt/heptane gradient from 0 to 25%) to give 1-benzenesulfonyl-4-(3-methoxy-propyl)-piperidine-4-carboxylic acid ethyl ester (4.15 g) as a yellow semi-solid. MS (ESI): 370.16 (MH+).

Workup

  1. customThe pyridine was evaporated off
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with 0,05M HCl and brine
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. customthe solvent was then removed in vacuo
  7. customthe crude oil was purified by flash chromatography over silica gel (AcOEt/heptane gradient from 0 to 25%)

Sources & evidence

ORD record
ord-f9520e1b16854fb49b97f54c52a3f677
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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