2-Pyridinemethanamine → HCID 16788272, compound

HRID 970898Notes

Reaction equation

HRID 970898 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-6cc4de88e3d2499fbdf81a6cc17e51cf
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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