Hydrochloric Acid → N-[3-(7-Methoxy-1-naphthyl)propyl]acetamide

HRID 2889

Reaction equation

HRID 2889 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][CH2:16][NH2:17])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:24](Cl)(=[O:26])[CH3:25].Cl>O>[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]2[CH2:14][CH2:15][CH2:16][NH:17][C:24](=[O:26])[CH3:25])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 190860083-(7-Methoxy-1-naphthyl)propylamine hydrochloride

Product 1

HCID 10220759N-[3-(7-Methoxy-1-naphthyl)propyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 0.005 mol (equivalent to 1.26 g) of 3-(7-methoxy-1-naphthyl)propylamine hydrochloride has been dissolved in 20 cm3 of water, 0.015 mol of potassium carbonate is added. The amine precipitates. Thereafter, 50 cm3 of chloroform are added and 0.010 mol of acetyl chloride is added dropwise. The medium is left stirring for 2 hours. It is acidified with 2N of hydrochloric acid and then stirred for 15 minutes. The aqueous phase is extracted with 3 times 50 cm3 of chloroform. The organic phases are washed with water, dried over calcium chloride and evaporated. Purification of the products is performed either by recrystallization or by column chromatography.

Workup

  1. customThe amine precipitates
  2. additionThereafter, 50 cm3 of chloroform are added
  3. waitThe medium is left
  4. stirringstirred for 15 minutes
  5. extractionThe aqueous phase is extracted with 3 times 50 cm3 of chloroform
  6. washThe organic phases are washed with water
  7. dry with materialdried over calcium chloride
  8. customevaporated
  9. customPurification of the products
  10. customis performed either by recrystallization or by column chromatography

Sources & evidence

ORD record
ord-23a827758ec74998ac781f9b6412b1c4
Source dataset
uspto-grants-1998_03
Patent number
US05731352

Linked notes

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