Chloride → HCID 10244203, compound

HRID 725910Notes

Reaction equation

HRID 725910 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH2:13][CH2:14][NH2:15].C(N(CC)CC)C.[OH-].[K+].[C:25](Cl)(=[O:28])[CH2:26][CH3:27].[Cl-]>ClCCl.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH2:13][CH2:14][NH:15][C:25](=[O:28])[CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 312ChlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 62324Propionyl chlorideHCID 118201402-(2-methoxy-1-naphthyl)ethanamine(SALTDATA: HCl)

Product 1

HCID 10244203HCID 10244203, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.40 g (6.96 mmol) of 2-(2-methoxynaphthyl)ethylamine, which is solubilized in 20 cm3 of anhydrous dichloromethane, are introduced into a 100-cm3 two-necked flask under an inert atmosphere. The mixture is cooled with an ice bath and stirred, and 1.5 cm3 (10.4 mmol) of triethylamine dried over potassium hydroxide and 0.7 cm3 (8.056 mmol) of propanoyl chloride are introduced. After the introduction of the reactants, the ice bath is removed and reaction is allowed to proceed at room temperature for 30 min. Hydrolysis of the excess chloride is carried out by pouring the reaction mixture into water. After extraction three times with dichloromethane, the organic phase is dried over magnesium sulfate. After evaporation of the solvent and recrystallization of the solid obtained, in the heated state, in a pentane/ethyl acetate mixture, 0.70 g (2.72 mmol) of N-[2-(2-methoxy-1-naphthyl)ethyl]propionamide (white solid) is obtained, equivalent to a yield after purification of 39%. ##STR19##

Workup

  1. additionare introduced into a 100-cm3 two-necked flask under an inert atmosphere
  2. temperatureThe mixture is cooled with an ice bath
  3. additionare introduced
  4. customAfter the introduction of the reactants, the ice bath is removed
  5. customreaction
  6. extractionAfter extraction three times with dichloromethane
  7. dry with materialthe organic phase is dried over magnesium sulfate
  8. customAfter evaporation of the solvent and recrystallization of the solid
  9. customobtained, in the heated state, in a pentane/ethyl acetate mixture

Sources & evidence

ORD record
ord-3a4ba11ba2674329909e0effb0c973b6
Source dataset
uspto-grants-1998_01
Patent number
US05708020

Reaction notes

Loading…