Acetic Anhydride → Eslicarbazepine acetate

HRID 526678Notes

Reaction equation

HRID 526678 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.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:36](OC(=O)C)(=[O:38])[CH3:37]>O.ClCCl>[CH3:37][C:36]([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:38]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 9881504Eslicarbazepine

Product 1

HCID 179344Eslicarbazepine acetateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of eslicarbazepine (18 gm), triethylamine (8.5 gm), dimethylaminopyridine (0.1 gm), acetic anhydride (8.7 gm) and dichloromethane (90 mL) was stirred at about 20-25° C. for about 4 hrs. To the resulting solution water was added and resulting solution was stirred for about 15 minutes. Organic layer was separated and washed with 1 N HCl solution followed by washing with water. The solvent was distilled out completely. Ethyl acetate was added to the resulting residue followed by stirring at about 25-30° C. for about 3 hrs. The resulting solid was filtered, washed and dried to obtain the title compound (Yield: 80%; HPLC purity: 99.8%; Chiral purity: 99.3%; d0.9 50.7 μm, d0.5 17.3 μm, d0.1 6.0 μm).

Workup

  1. customresulting solution
  2. customOrganic layer was separated
  3. washwashed with 1 N HCl solution
  4. washby washing with water
  5. distillationThe solvent was distilled out completely
  6. additionEthyl acetate was added to the resulting residue
  7. stirringby stirring at about 25-30° C. for about 3 hrs
  8. filtrationThe resulting solid was filtered
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-8c407f0299db433fb98f9fc09cbb78ff
Source dataset
uspto-grants-2016_05
Patent number
US09346760B2

Reaction notes

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