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

HRID 2194128Notes

Reaction equation

HRID 2194128 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]#[N:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]#[N:14])[CH2:7][CH2:8][N:9]([S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[Cl:15])(=[O:24])=[O:23])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 59577916ethyl 1-Cyanomethyliso-nipecotate

Product 1

HCID 595780111-(2-Chloro-benzenesulfonyl)-4-cyanomethyl-piperidine-4-carboxylic acid ethyl esterYield 31.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Cyanomethyl-piperidine-4-carboxylic acid ethyl ester (14.2 g) was dissolved in pyridine (150 ml), 2-chlorobenzenesulfonyl chloride (16.83 g) was added and the reaction mixture was stirred overnight at RT. Then, most of pyridine was evaporated off in vacuo, the residue was dissolved in AcOEt, washed with 0.5M aqueous HCl and brine. The organic layer was dried over magnesium sulphate and concentrated in vacuo. The residue (crude oil) was chromatographed over silica (AcOEt/Heptanes, gradient from 0 to 25%) to give the desired material (8.5 g) as viscous brown oil. MS (ESI): 388.1 (M+NH4)+.

Workup

  1. customThen, most of pyridine was evaporated off in vacuo
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with 0.5M aqueous HCl and brine
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue (crude oil) was chromatographed over silica (AcOEt/Heptanes, gradient from 0 to 25%)

Sources & evidence

ORD record
ord-fe3965627f044330a77ea17570175f23
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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