Sodium Iodide → 4-(2-Chlorophenyl)-4-fluoropiperidine

HRID 2265150Notes

Reaction equation

HRID 2265150 reaction equation
C[Si](C)(C)Cl.[I-].[Na+].C(#N)C.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1([F:34])[CH2:23][CH2:22][N:21](C(OCC2C=CC=CC=2)=O)[CH2:20][CH2:19]1>C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1([F:34])[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6342AcetonitrileHCID 6397Chlorotrimethylsilane2×HCID 23157020HCID 23157020, compound

Product 1

HCID 231570494-(2-Chlorophenyl)-4-fluoropiperidineYield 76.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.53 mL of trimethylchlorosilane and 1.82 g of sodium iodide were added to acetonitrile (50 mL) solution of 2.11 g of benzyl 4-(2-chlorophenyl)-4-fluoropiperidine-1-carboxylate, and stirred at room temperature for 30 minutes. 0.77 mL of trimethylchlorosilane and 0.91 g of sodium iodide were further added thereto, and stirred for 10 minutes. Then, the reaction liquid was diluted with ethyl acetate, and back-extracted with 1 M hydrochloric acid. Sodium hydroxide was added to the aqueous layer so that the system was made basic, and then extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol=10/1) to obtain 992 mg of the entitled compound as a colorless oily substance.

Workup

  1. stirringstirred for 10 minutes
  2. customThen, the reaction liquid
  3. extractionback-extracted with 1 M hydrochloric acid
  4. additionSodium hydroxide was added to the aqueous layer so that the system
  5. extractionextracted with chloroform
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. customthe residue was separated
  9. custompurified through silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-a6fa3b1998574815afdfb0aeda878d66
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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