Triethylamine → 4-[3-(2-Ethylhexanoylamino)propylthio]pyridine hydrochloride

HRID 6098

Reaction equation

HRID 6098 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([Cl:26])=[O:25])[CH3:22]>C(Cl)Cl>[ClH:26].[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 791032-Ethylhexanoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190791914-[3-(2-Ethylhexanoylamino)propylthio]pyridine hydrochlorideYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 800 mg (3.32 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.22 ml (15.9 mmol) of triethylamine in 30 ml of methylene chloride was added 0.69 ml (3.98 mmol) of 2-ethylhexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.02 g of the desired compound (free base) (quant., pale yellow oil).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-98d9895ba86346508f59e97bf0b9a4d2
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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