Chloroform → HCID 22115872, compound

HRID 1276479Notes

Reaction equation

HRID 1276479 reaction equation
[C:1]1([C:7]([O:25][Si](C)(C)C)=[CH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14](=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:30]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].C(Cl)(Cl)[Cl:44]>O1CCCC1>[ClH:44].[Br:30][CH:8]([C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:25])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14](=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 53909427HCID 53909427, compound

Product 1

HCID 22115872HCID 22115872, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

6.21 g of 1-(4-phenyl-4-trimethylsilyloxy-3-buten-1-yl)-4-(4-fluorobenzylidene)piperidine was dissolved in 30 ml of tetrahydrofuran, and 2.83 g of N-bromosuccinimide was added in small portions to the thus prepared solution which was cooled at -50° C. The reaction mixture was further stirred at -50° C. for 1 hour and gradually warmed to -20° C., and then thereto was added saturated aqueous sodium bicarbonate and chloroform, subsequently separating the organic layer. The aqueous layer was further extracted with chloroform, and the organic layers were combined and washed with water. After drying over anhydrous magnesium sulfate, the drying agent was removed by filtration, and 8 ml of 4 N hydrogen chloride dioxane solution was added to the resulting filtrate which was cooled in an ice bath. The solvent was evaporated under reduced pressure, and the resulting residue was crystallixed from ether to obtain 6.00 g of 1-(3-bromo-4-phenyl-4-oxobutyl)-4-(4-fluorobenzylidene)piperidine hydrochloride.

Workup

  1. temperaturegradually warmed to -20° C.
  2. customsubsequently separating the organic layer
  3. extractionThe aqueous layer was further extracted with chloroform
  4. washwashed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe drying agent was removed by filtration, and 8 ml of 4 N hydrogen chloride dioxane solution
  7. additionwas added to the resulting filtrate which
  8. temperaturewas cooled in an ice bath
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8d52d8b118b847d19778ba009e355c6a
Source dataset
uspto-grants-2000_12
Patent number
US06166033

Reaction notes

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