Phenethylamine → 2-[Benzyl(methyl)amino]pyridine-4-carboxylic acid

HRID 2223739Notes

Reaction equation

HRID 2223739 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:11](CN)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:20]([N:22](CC)CC)C>C(Cl)Cl>[CH2:11]([N:22]([CH3:20])[C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([OH:10])=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 226433412-[Benzyl(methyl)amino]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-pyridine-4-carboxylic acid (300 mg, 1.9 mmol), benzylmethylamine (230 mg, 1.9 mmol) and triethylamine (192 mg, 1.9 mmol) is heated at 120° C. for 12 h. The residue is dissolved in CH2Cl2 (30 mL) and extracted with 1M aqueous NaOH (3×5 mL). The aqueous layer is adjusted to pH 1-2 with 12N aqueous HCl and extracted with EtOAc (6×5 mL). The organic extracts are combined, dried (MgSO4), and evaporated to provide the title compound.

Workup

  1. extractionextracted with 1M aqueous NaOH (3×5 mL)
  2. extractionextracted with EtOAc (6×5 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3c9bf81f05054c0fa46e4fcd2ccec058
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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