Sodium Iodide → HCID 11779386, compound

HRID 1961635Notes

Reaction equation

HRID 1961635 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[Na+]>C(#N)C>[CH2:24]([N:12]1[CH2:13][CH2:14][CH:9]([C:7]([C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:16][CH:15]=2)=[O:8])[CH2:10][CH2:11]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 11779386HCID 11779386, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(3 g, 12.3 mmol) of 4-(4-fluorobenzoyl)piperidine hydrochloride was suspended in acetonitrile (60 mL) and triethylamine (4.29 mL, 31 mmol), benzylbromide (1.61 mL, 14 mmol) and sodium iodide (2.8 g, 18 mol) were added. The mixture was stirred at 80° C. overnight and after cooling the mixture was filtrated, water was added and the aqueous phase was extracted with 100 mL of dichloromethane. The combined organic phases were dried with magnesium sulfate, filtrated concentrated and purified with column chromatography on silica using dichloromethane/Methanol (95/0.5) to yield 3.6 g, (12 mmol, 99% yield) of the title compound as a brown solid. MS (m/e): 298.4 (M+H+).

Workup

  1. temperatureafter cooling the mixture
  2. filtrationwas filtrated
  3. additionwater was added
  4. extractionthe aqueous phase was extracted with 100 mL of dichloromethane
  5. dry with materialThe combined organic phases were dried with magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. custompurified with column chromatography on silica

Sources & evidence

ORD record
ord-72684b2f1c1841b38486b8bcec882549
Source dataset
uspto-grants-2013_04
Patent number
US08415350B2

Reaction notes

Loading…