Hydrochloric Acid → Eslicarbazepine acetate

HRID 526679Notes

Reaction equation

HRID 526679 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.CN(C1C=CC=CN=1)C.[C:29](OC(=O)C)(=[O:31])[CH3:30].Cl>O.ClCCl.C(N(CC)CC)C>[CH3:30][C:29]([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:31]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 9881504Eslicarbazepine

Product 1

HCID 179344Eslicarbazepine acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of eslicarbazepine (30 gm), triethylamine (19.7 gm), dimethylaminopyridine (0.15 gm), and dichloromethane (150 mL), acetic anhydride (14.5 mL in 14.5 mL dichloromethane) was added and solution was stirred at about 20-25° C. for about 3 hrs. The resulting solution was cooled to about 10-15° C. To the resulting solution water (90 mL) was added followed by addition of HCl till pH of the resulting solution was 1-2. Organic layer was separated and washed with water. Water was added to organic layer followed by cooling to about 10-15° C. The pH of the resulting solution was adjusted to 9-10 by adding NaOH (10% w/v) solution. Organic layer was separated and solvent was distilled out completely to obtain the title compound.

Workup

  1. temperatureThe resulting solution was cooled to about 10-15° C
  2. customOrganic layer was separated
  3. washwashed with water
  4. additionWater was added to organic layer
  5. temperatureby cooling to about 10-15° C
  6. additionby adding NaOH (10% w/v) solution
  7. customOrganic layer was separated
  8. distillationsolvent was distilled out completely

Sources & evidence

ORD record
ord-f5b8673a21564b17a1acbf6fdb988e98
Source dataset
uspto-grants-2016_05
Patent number
US09346760B2

Reaction notes

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