Pyridine → Eslicarbazepine acetate

HRID 526682Notes

Reaction equation

HRID 526682 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:16]([NH2:18])=[O:17])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C@@H:8]([OH:19])[CH2:7][C:5]=2[CH:6]=1.N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[C:35](Cl)(=[O:37])[CH3:36]>ClCCl.C(OCC)(=O)C>[CH3:36][C:35]([O:19][C@@H:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[N:15]([C:16]([NH2:18])=[O:17])[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[CH2:7]1)=[O:37]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 218852-DimethylaminopyridineHCID 9881504Eslicarbazepine

Product 1

HCID 179344Eslicarbazepine acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
37.5 °C

Procedure

A solution of eslicarbazepine (15.0 gm), pyridine (8 mL), dimethylaminopyridine (0.17 gm) in dichloromethane (150 mL) was cooled to 5-10° C. Added acetyl chloride (7.6 mL) at about 5-10° C. followed by stirring at 35-40° C. for about 5-6 h. Washed the reaction mass with 0.5N HCl solution (45 mL) and followed by washing the organic layer with water (100 mL). Distilled out the solvent completely under vacuum to obtain crude eslicarbazepine acetate. The residue was dissolved in a mixture (60 mL) of dichloromethane and ethyl acetate (1:1) at 35-40° C. then cooled to 25-30° C. Reaction mass was filtered, washed with ethyl acetate and dried to obtain the title compound (m. p. 186.0-187.2° C.).

Workup

  1. customat about 5-10° C.
  2. washWashed the reaction mass with 0.5N HCl solution (45 mL)
  3. washby washing the organic layer with water (100 mL)
  4. distillationDistilled out the solvent completely under vacuum
  5. customto obtain crude eslicarbazepine acetate
  6. temperaturethen cooled to 25-30° C
  7. customReaction mass
  8. filtrationwas filtered
  9. washwashed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-9bce303e8a53461c951450c61779bf60
Source dataset
uspto-grants-2016_05
Patent number
US09346760B2

Reaction notes

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