Potassium Iodide → 1-(Diphenylmethyl)pyrrolidine

HRID 80318

Reaction equation

HRID 80318 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[I-].[K+].C(=O)([O-])O.[Na+]>CO.C(#N)C>[C:3]1([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7035ChlorodiphenylmethaneHCID 31268PyrrolidineHCID 516892Sodium Bicarbonate

Product 1

HCID 2450121-(Diphenylmethyl)pyrrolidineYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Chlorodiphenylmethane (0.50 g, 2.47 mmol) (Wako Pure Chemical Industries, Ltd.), pyrrolidine (0.53 g, 7.45 mmol) (Tokyo Chemical Industry Co., Ltd.), and potassium iodide (0.10 g, 0.60 mmol) (Wako Pure Chemical Industries, Ltd.) were added to acetonitrile (20 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 2 hours. The mixture was allowed to cool to room temperature. After that, 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 subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.36 g, 61% yield).

Workup

  1. temperaturethe mixture was refluxed for 2 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

Sources & evidence

ORD record
ord-538c707c4b594608ab700e0bee2c52fc
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Linked notes

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