Hexane → HCID 13180319, compound

HRID 2107378Notes

Reaction equation

HRID 2107378 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9](C)[CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:23]1([O:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCCCCC>C1(C)C=CC=CC=1>[O:29]([C:30]([N:9]1[CH2:10][CH2:11][CH:6]([C:4](=[O:5])[C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[F:1])[CH2:7][CH2:8]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 131803174-(2-Fluorobenzoyl)-1-methylpiperidine

Product 1

HCID 13180319HCID 13180319, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 57.5 g of 4-(2-fluorobenzoyl)-1-methyl piperidine and 68.7 g of potassium carbonate in 750 ml of toluene was added with stirring 47 g of phenylchloroformate. The reaction mixture was heated under reflux for 5 hrs, cooled to room temperature, filtered, and the solvent removed under reduced pressure to give an oil. Trituration of the oil with hexane gave 48.6 g (46%) of product. Recrystallization of 1.0 g of product from ethanol-water (2x) and from ethanol gave the analytical sample, mp 95°-96° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customto give an oil

Sources & evidence

ORD record
ord-d955c4ace3d64c3b90cb4d7d27b26423
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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