Benzenesulfonyl chloride → HCID 66787540, compound

HRID 2194003Notes

Reaction equation

HRID 2194003 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 AcOEt 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 AcOEt
  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-92a77f5131bf493fa6803e2a8302b58b
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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