Methyl(2-(pyrrolidin-1-yl)ethyl)amine → 6-Chloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamide

HRID 748518

Reaction equation

HRID 748518 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:13]([CH3:12])[CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 632074446-Chloro-N-methyl-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-chloropyridine-3-sulfonylchloride (636 mg, 3 mmol; described in: Naegeli, C. et al. Helv. Chim. Actal. 1938, 21, 1746-1750) in methylene chloride (10 mL) was added methyl-(2-pyrrolidin-1-ylethyl)amine (384 mg, 3 mmol; described in: J. Amer. Chem. Soc. 1955, 77, 3632-3634) dissolved in methylene chloride (10 mL) dropwise. The reaction mixture was stirred over night at room temperature followed by the extraction with aqueous HCl (3%). The acidic water layer was alkalized with an aqueous saturated solution of NaHCO3 and extracted with methylene chloride. The organic phase was dried (Na2SO4) and evaporated in vacuo to give 0.75 gram (80% yield) of the title compound: MS (ES) m/z 304 (M++1).

Workup

  1. extractionfollowed by the extraction with aqueous HCl (3%)
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f74ad4236f434ba7ac93b1a8c2dd5aec
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Linked notes

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