Dimethylformamide → HCID 15656840, compound

HRID 2396004Notes

Reaction equation

HRID 2396004 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.Cl.[NH2:25][CH:26]1[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1>C(Cl)Cl.C1(C)C=CC=CC=1.[OH-].[Na+]>[N:28]12[CH2:33][CH2:32][CH:31]([CH2:30][CH2:29]1)[CH:26]([NH:25][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[CH3:1])[CH2:27]2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 117822,3-Dimethylbenzoic acidHCID 65578Oxalyl chlorideHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 15656840HCID 15656840, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,3-dimethylbenzoic acid (5.0 g; 33.3 mmol), oxalyl chloride (40.0 mmol, 3.5 mL) and dimethylformamide (0.1 mL) were dissolved in methylene chloride (100 mL). The mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. A solution of the concentrate in toluene (100 mL) was added dropwise to a stirred solution of (RS)-3-amino-1-azabicyclo[2.2.2]octane dihydrochloride (7.0 g; 35 mmol)in toluene (50 mL) and NaOH (2.0N, 50 mL) at 0° C. The reaction mixture was maintained at 0° C. and stirred for 30 minutes. The aqueous layer was extracted with of toluene (2×50 mL) and the combined organic layers dried over magnesium sulfate. Removal of the solvent under reduced pressure gave (RS)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dimethylbenzamide as a white solid (5.5 g, 25.4 mmol), m.p. 160°-161° C. The hydrochloride salt is prepared from ethanol-hydrogen chloride.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationA solution of the concentrate in toluene (100 mL)
  3. temperatureThe reaction mixture was maintained at 0° C.
  4. stirringstirred for 30 minutes
  5. extractionThe aqueous layer was extracted with of toluene (2×50 mL)
  6. dry with materialthe combined organic layers dried over magnesium sulfate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2253bca0e6e447f08b2be06548d7489d
Source dataset
uspto-grants-1996_02
Patent number
US05491148

Reaction notes

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