Triethylamine → 4-(3-(cinnamoylamino)propylthio]pyridine Hydrochloride

HRID 6103

Reaction equation

HRID 6103 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.[C:21]([Cl:31])(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[ClH:31].[C:21]([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:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 676532314-(3-(cinnamoylamino)propylthio]pyridine HydrochlorideYield 88.8%

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 830 mg (4.98 mmol) of cinnamoyl 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: methanol/ethyl acetate=1:10) to obtain the powder which was washed with ether and dried to obtain 1.10 g of the desired compound (free base) (88.8%, colorless powder), mp: 116.0°-11.7° 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: methanol/ethyl acetate=1:10)
  7. customto obtain the powder which
  8. washwas washed with ether
  9. customdried

Sources & evidence

ORD record
ord-f15dd3fd1fd04d268953342d248889ee
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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