Trityl chloride → Trifenmorph

HRID 80304Notes

Reaction equation

HRID 80304 reaction equation
[NH:1]1[CH2:6][CH2:5][O: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(OCC)(=O)C.CN(C)C=O>[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][O:4][CH2:3][CH2:2]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 14993TrifenmorphYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Morpholine (0.47 g, 5.39 mmol) (Wako Pure Chemical Industries, Ltd.), triphenylchloromethane (1.50 g, 5.39 mmol) (Wako Pure Chemical Industries, Ltd.), and potassium carbonate (0.75 g, 5.39 mmol) (Wako Pure Chemical Industries, Ltd.) were added to N,N-dimethylformamide (5 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was stirred at room temperature overnight. 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, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.):ethyl acetate (Wako Pure Chemical Industries, Ltd.)=9:1 as an eluent), to thereby obtain the title compound (0.42 g, 71% yield).

Workup

  1. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c0f99affef1f48fd81ebc2324c5e2843
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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