2-Pyridinemethanamine → HCID 16788272, compound

HRID 2308276Notes

Reaction equation

HRID 2308276 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Cl[S:10]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17])(=[O:12])=[O:11]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][S:10]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 16788272HCID 16788272, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a pre-cooled (ice bath) solution of 2-(aminomethyl)-pyridine (1.05 g, 9.7 mmol) in anhydrous CH2Cl2 (15 ml) was added 3-(Chlorosulfonyl) benzoic acid (714 mg, 3.23 mmol) under N2 and the ice bath was removed after addition. Stirring was continued for 18 hours at room temperature, and the reaction mixture was diluted with 300 ml CH2Cl2, and filtered through celite. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, using 3:6:91 CH3COOH—MeOH—CH2Cl2, gave the title compound (840 mg, 89%) as a pure white solid.

Workup

  1. customthe ice bath was removed
  2. additionafter addition
  3. additionthe reaction mixture was diluted with 300 ml CH2Cl2
  4. filtrationfiltered through celite
  5. customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1e23285655394a3fb0cb27961f33a9d9
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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