Potassium Carbonate → HCID 2772320, compound

HRID 2082131Notes

Reaction equation

HRID 2082131 reaction equation
[C:1]1(=[O:13])[NH:9][C:8](=[O:10])[CH:7]2[CH2:11][CH2:12][C:2]1([C:4]2([CH3:6])[CH3:5])[CH3:3].[Br-].[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:30][CH2:29][N+:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][N:9]2[C:8](=[O:10])[CH:7]3[C:4]([CH3:6])([CH3:5])[C:2]([CH3:3])([CH2:12][CH2:11]3)[C:1]2=[O:13])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 160771,8,8-Trimethyl-3-aza-bicyclo[3.2.1]octane-2,4-dioneHCID 658423142348-17-2

Product 1

HCID 2772320HCID 2772320, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.07 g (0.0225 mol) of DL-camphorimide (II), 6.71 g (0.0225 mol) of 8-(2-pyridyl)-8-aza-5-azoniaspiro[4,5]-decane bromide (III) and 3.73 g (0.027 mol) of potassium carbonate was refluxed in 80 ml of absolute dimethylformamide for 24 hours, then the resulting mixture was cooled, filtered, and dimethylformamide was distilled off under reduced pressure. The residue was dissolved in 100 ml of 5% HCl, the resulting solution was extracted twice with 50 ml of ether to remove impurities of non-basic nature, and saturated with soda. The precipitated base was extracted with ethyl acetate, the extract was dried with potassium carbonate and purified by passing through a column packed with a neutral aluminum oxide 5 cm thick (with ethyl acetate as eluent). After the solvent was distilled off, there was obtained a free base in the form of an oil which was then crystallized. Mp. 96°-97° C.

Workup

  1. temperaturethe resulting mixture was cooled
  2. filtrationfiltered
  3. distillationdimethylformamide was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in 100 ml of 5% HCl
  5. extractionthe resulting solution was extracted twice with 50 ml of ether
  6. customto remove impurities of non-basic nature
  7. extractionThe precipitated base was extracted with ethyl acetate
  8. dry with materialthe extract was dried with potassium carbonate
  9. custompurified
  10. distillationAfter the solvent was distilled off
  11. customthere was obtained a free base in the form of an oil which
  12. customwas then crystallized

Sources & evidence

ORD record
ord-6f1f677bfa544e6b87dd1454ef34d75b
Source dataset
uspto-grants-1993_02
Patent number
US05187277

Reaction notes

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