Sodium Carbonate → 5-[4-(9-Xanthenylidene)piperidino]-2-pentanone

HRID 616217

Reaction equation

HRID 616217 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[CH:8]1[C:21]2[C:20](=[C:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH:18]1[C:19]2[C:20](=[C:22]3[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6])[CH2:24][CH2:23]3)[C:21]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:13][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 774932-Pentanone, 5-bromo-HCID 157805164-(9-Xanthenylidene)piperidine

Product 1

HCID 203715285-[4-(9-Xanthenylidene)piperidino]-2-pentanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

7.2 g of 5-bromo-2-pentanone in 50 cc of chloroform are added dropwise to a suspension of 10.0 g of 4-(9-xanthenylidene)piperidine [M.P. 147°-149°, produced from N-methyl-4-(9-xanthenylidene)piperidine] and 9.25 g of sodium carbonate in 200 cc of chloroform. The reaction mixture is boiled at reflux for 17 hours, is filtered, concentrated by evaporation, the evaporation residue is placed on a column of 100 g of silica gel and elution is effected with chloroform containing 1% of methanol. The evaporation residue of the eluate is dissolved in acetone and made weakly acid to Congo red with hydrogen chloride in ether. The 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately is recrystallized from alcohol. M.P. 248°-251° (decomp.).

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationis filtered
  3. concentrationconcentrated by evaporation
  4. washthe evaporation residue is placed on a column of 100 g of silica gel and elution
  5. dissolutionThe evaporation residue of the eluate is dissolved in acetone
  6. customThe 5-[4-(9-xanthenylidene)piperidino]-2-pentanone hydrochloride which precipitates immediately
  7. customis recrystallized from alcohol

Sources & evidence

ORD record
ord-47ac54bf25334b349e0ffafc2ca17317
Source dataset
uspto-grants-1978_02
Patent number
US04072756

Linked notes

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