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

HRID 2210107Notes

Reaction equation

HRID 2210107 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.[CH:21]1([C:27]([Cl:29])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl>[ClH:29].[CH:21]1([C:27]([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:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Product 1

HCID 190792424-[3-(Cyclohexanoylamino)propylthio]pyridine hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.66 ml (4.96 mmol) of cyclohexanoyl 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 890 mg of the desired compound (free base) (77.0% colorless prisms), mp: 93.0°-94.0° 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-199c6c775751499988de858594ff4cd1
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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