Chloride → HCID 9970416, compound

HRID 1451548Notes

Reaction equation

HRID 1451548 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:29])[CH2:26][CH2:27][CH3:28].[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:29])[CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 5

HCID 312ChlorideHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 14797Potassium HydroxideHCID 118201402-(2-methoxy-1-naphthyl)ethanamine(SALTDATA: HCl)

Product 1

HCID 9970416HCID 9970416, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.45 g (2.23 mmol) of 2-(2-methoxy-1-naphthyl)ethylamine, which is solubilized in 20 cm3 of anhydrous dichloromethane, is introduced into a 100-cm3 two-necked flask under an inert atmosphere. The mixture is cooled with an ice bath and stirred, and 0.47 cm3 (3.37 mmol) of triethylamine dried over potassium hydroxide is introduced, followed by 0.28 cm3 (2.69 mmol) of butyryl chloride. 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, 0.29 g (1.07 mmol) of N-[2-(2-methoxynaphthyl)ethyl]butyramide (white solid) is obtained, equivalent to a yield after purification of 48%.

Workup

  1. additionis introduced into a 100-cm3 two-necked flask under an inert atmosphere
  2. temperatureThe mixture is cooled with an ice bath
  3. additionis 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-ffd1c0b70f1f4e47a6bd3559a1df2385
Source dataset
uspto-grants-1997_02
Patent number
US05604261

Reaction notes

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