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Sodium Hydroxide → 3-(2-Chloro-10,11-dihydro-dibenzo[b,f]oxepin-10-yl)-8-methyl-3,8-diazabicyclo(3.2.1)octane monomaleate

HRID 618441
Notes
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Reaction equation

HRID 618441 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9](Cl)[CH2:10][C:4]=2[CH:3]=1.Cl.Cl.[CH3:20][N:21]1[CH:26]2[CH2:27][CH2:28][CH:22]1[CH2:23][NH:24][CH2:25]2.[C:29](=[O:32])([OH:31])[O-].[Na+].[OH-:34].[Na+]>CCOCC.CN(C)C=O>[C:5]([OH:34])(=[O:6])/[CH:4]=[CH:10]\[C:29]([OH:31])=[O:32].[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]([N:24]3[CH2:25][CH:26]4[N:21]([CH3:20])[CH:22]([CH2:28][CH2:27]4)[CH2:23]3)[CH2:10][C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 221201882,10-Dichloro-10,11-dihydro-dibenz[b,f]oxepinHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Product 1

HCID 867545003-(2-Chloro-10,11-dihydro-dibenzo[b,f]oxepin-10-yl)-8-methyl-3,8-diazabicyclo(3.2.1)octane monomaleate

Reagents, catalysts & solvents

2
HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,10-Dichloro-10,11-dihydro-dibenz[b,f]oxepin (3.2 g), 8-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride (1.6 g), sodium bicarbonate (10 g), and dimethylformamide (40 mL) was stirred at 100° C. for 1 h. After cooling, the reaction mixture was poured onto water, made basic with NaOH and the products are extracted with ether. The ether layer was extracted with 3N HCl, the aqueous layer is basified and the basic product was reextracted with ether. After drying over magnesium sulfate the solvent was removed in vacuo. The residue is dissolved in ethanol and 500 mg of maleic acid was added and the mixture was warmed until a clear solution is obtained. After dilution of this mixture with ether and cooling at -20° C. overnight, 3-(2-Chloro-10,11-dihydro-dibenzo[b,f]oxepin-10-yl)-8-methyl-3,8-diazabicyclo(3.2.1)octane monomaleate (Compound 1) melting at 169-170° C. was obtained as white crystals.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto water
  3. extractionthe products are extracted with ether
  4. extractionThe ether layer was extracted with 3N HCl
  5. dry with materialAfter drying over magnesium sulfate the solvent
  6. customwas removed in vacuo
  7. dissolutionThe residue is dissolved in ethanol
  8. addition500 mg of maleic acid was added
  9. temperaturethe mixture was warmed until a clear solution
  10. customis obtained

Sources & evidence

ORD record
ord-8c5be94a0b4f4c65ad1bd6e86a3f4be5
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05952501

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes