Acetyl chloride → Agomelatine

HRID 572700Notes

Reaction equation

HRID 572700 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1.[C:16](Cl)(=[O:18])[CH3:17]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 110526677-Methoxy-1-naphthaleneethanamine

Product 1

HCID 82148AgomelatineYield 99.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

40 g 2-(7-methoxy-1-naphthyl)ethylamine was dissolved in 250 ml pyridine and heated to 40° C. for complete dissolution. 21.9 g acetyl chloride was slowly added in drops with stirring in ice bath. After completion of addition, the ice bath was removed and the solution was stirred at room temperature for 30 min. Subsequently, the reaction solution was poured into 300 ml ice water together with vigorous stirring, resulting in a large amount of white precipitate being precipitated. The stirring was carried out for another 1 hour. Then, the solution was filtered and the filter cake was washed by 200 ml×2 water to obtain 48 g crude product (which was used in the following preparation examples).

Workup

  1. additionAfter completion of addition
  2. customthe ice bath was removed
  3. stirringthe solution was stirred at room temperature for 30 min
  4. additionSubsequently, the reaction solution was poured into 300 ml ice water together with vigorous stirring
  5. customresulting in a large amount of white precipitate
  6. custombeing precipitated
  7. filtrationThen, the solution was filtered
  8. washthe filter cake was washed by 200 ml×2 water

Sources & evidence

ORD record
ord-cc360fe48a4f4cecae0b669ae9fffe01
Source dataset
uspto-grants-2015_05
Patent number
US09029420B2

Reaction notes

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