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Potassium Hydroxide → 5-Aminosulfonyl-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-methoxybenzamide Hydrochloride Hydrate

HRID 364634
Notes
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Reaction equation

HRID 364634 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[OH-].[K+].NC1C2CCN(CC2)C1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:31]([S:34](=[O:37])(=[O:36])[NH2:35])=[CH:30][C:26]=1[C:27]([Cl:29])=[O:28]>O.O1CCCC1>[OH2:24].[ClH:29].[NH2:35][S:34]([C:31]1[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[C:26]([CH:30]=1)[C:27]([NH:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1)=[O:28])(=[O:36])=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 1042285-(Aminosulphonyl)-2-methoxybenzoyl chlorideHCID 1232383-AminoquinuclidineHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 202393685-Aminosulfonyl-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-methoxybenzamide Hydrochloride Hydrate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminoquinuclidine dihydrochloride (2.5 g, 0.0126 mole) in 25 ml of water was treated with approximately 5 g of KOH and the resultant slurry/solution taken to complete dryness on the rotary evaporator at 50°/35 mm. The dry residue was carefully extracted by repeated triturations with warm tetrahydrofuran until a total volume of 130 ml had been collected and dried over magnesium sulfate. This solution of 3-aminoquinuclidine base was treated with a solution of 2-methoxy-5-sulfamylbenzoyl chloride (2.92 g, 0.0117 mole) in 50 ml of dry tetrahydrofuran by dropwise addition under nitrogen. The resultant very turbid solution was refluxed gently for about 30 min, then freed of tetrahydrofuran by allowing it to evaporate. The residue was taken up in 90% ethanol containing a few drops of ethereal hydrogen chloride, filtered and chilled. The solid produced was then recrystallized again to yield 4.3 g (97%), m.p. 233°-234° C. NMR, MS, and IR were in support of the structure proposed.

Workup

  1. customthe resultant slurry/solution taken to complete dryness on the rotary evaporator at 50°/35 mm
  2. extractionThe dry residue was carefully extracted
  3. customhad been collected
  4. dry with materialdried over magnesium sulfate
  5. temperatureThe resultant very turbid solution was refluxed gently for about 30 min
  6. customto evaporate
  7. filtrationfiltered
  8. temperaturechilled
  9. customThe solid produced
  10. customwas then recrystallized again
  11. customto yield 4.3 g (97%), m.p. 233°-234° C

Sources & evidence

ORD record
ord-ec7aeb374982460d9ec68512f9989070
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04605652

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes