Trityl chloride → 1-Tritylpiperidine

HRID 80301Notes

Reaction equation

HRID 80301 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(#N)C>[C:7]1([C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 153723441-TritylpiperidineYield 31.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperidine (1.50 g, 17.6 mmol) (Wako Pure Chemical Industries, Ltd.), triphenylchloromethane (5.40 g, 19.4 mmol) (Wako Pure Chemical Industries, Ltd.), and potassium carbonate (2.68 g, 19.4 mmol) (Wako Pure Chemical Industries, Ltd.) were added to acetonitrile (30 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 5 hours. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of chloroform (Wako Pure Chemical Industries, Ltd.) and n-hexane (Wako Pure Chemical Industries, Ltd.), to thereby obtain the title compound (1.80 g, 31% yield).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of chloroform (Wako Pure Chemical Industries, Ltd.) and n-hexane (Wako Pure Chemical Industries, Ltd.)

Sources & evidence

ORD record
ord-cafab86e72a84615b19f241dc9979573
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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