Triethylamine → 4-[3-(4-n-Butoxybenzoylamino)propylthio]pyridine hydrochloride

HRID 2210119Notes

Reaction equation

HRID 2210119 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]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([Cl:32])=[O:31])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[ClH:32].[CH2:21]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:31])=[CH:33][CH:34]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190791454-[3-(4-n-Butoxybenzoylamino)propylthio]pyridine hydrochlorideYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 0.94 ml (4.96 mmol) of 4-n-butoxybenzoyl 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 1.10 g of the desired compound (free base) (76.9%, colorless powder), mp: 98.0°-99.0° C.

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-f263731dce8d42c2b1893c90f46e6961
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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