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Boron trifluoride etherate → 10,11-dihydro-10-methoxycarbonylpropylimino-5H-dibenz[b,f]azepine-5-carboxamide

HRID 361323
Notes
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Reaction equation

HRID 361323 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1.Cl.[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][NH2:27].B(F)(F)F.CCOCC>C1(C)C(C)=CC=CC=1>[CH3:21][O:22][C:23]([CH2:24][CH2:25][CH2:26][N:27]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1)=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 34312OxcarbazepineHCID 27563834-Aminobutyric acid methyl ester hydrochloride

Product 1

HCID 5715571810,11-dihydro-10-methoxycarbonylpropylimino-5H-dibenz[b,f]azepine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
135 °C

Procedure

To a suspension of 0.2 g (0.79 mmol) of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide and 0.1 g (0.67 mmol) of methyl-4-aminobutyrate hydrochloride in 5 mL of xylene was added 0.07 g (0.49 mmol) of boron trifluoride diethyl etherate. The resulting mixture was heated at 135° C. for seven hours and then allowed to cool to room temperature. The mixture was then filtered and the residue was extracted with toluene. The combined extracts were evaporated under reduced pressure and the residue chromatographed on silica gel using a 4:1 mixture of petroleum ether-ethyl acetate. Chromatographically homogenous fractions were pooled and the solvents were removed under reduced pressure to give the desired product as a yellow oil which crystallised on standing to give yellow crystals which decomposed on heating without melting.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was then filtered
  3. extractionthe residue was extracted with toluene
  4. customThe combined extracts were evaporated under reduced pressure
  5. customthe residue chromatographed on silica gel using
  6. additiona 4:1 mixture of petroleum ether-ethyl acetate
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-711b24ff6bee4af983e5f51cecb84810
Source dataset
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05866566

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes