Triethylamine → 4-[3-(Propionylamino)propylthio]pyridine

HRID 274630Notes

Reaction equation

HRID 274630 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)(=[O:24])[CH2:22][CH3:23]>C(Cl)Cl>[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:24])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 152952564-[3-(Propionylamino)propylthio]pyridineYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 700 mg (2.90 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 1.62 ml (11.6 mmol) of triethylamine in 30 ml of methylene chloride was added 0.30 ml (3.48 mmol) of propionyl chloride and the mixture was stirred at room temperature for 30 minutes. The reaction solution 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 483 mg of the desired compound (74.2%, yellow prisms), mp: 50.0°-51.0° C.

Workup

  1. washThe reaction solution was washed with an aqueous saturated sodium bicarbonate solution and water
  2. customdried
  3. distillationThe solvent was distilled off
  4. customThe residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10)
  5. customto obtain the powder which
  6. washwas washed with ether
  7. customdried

Sources & evidence

ORD record
ord-621bf2c773a34751ba4821d4a1339f00
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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