Potassium Iodide → 3-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

HRID 278919

Reaction equation

HRID 278919 reaction equation
Cl.[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].Br[CH2:17][CH2:18][CH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[C:22]2[C:23]([NH:25][C:26](=[O:27])[C:21]=12)=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][N:7]([CH2:17][CH2:18][CH2:19][C:20]2[CH:30]=[CH:29][CH:28]=[C:22]3[C:23]([NH:25][C:26](=[O:27])[C:21]=23)=[O:24])[CH2:8][CH2:9]1)#[N:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochlorideHCID 21958088Bromopropylphthalimide

Product 1

HCID 227252233-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 4-cyano-4-phenylpiperidine hydrochloride (111 g, 0.5 mol), 3-bromopropylphthalimide (135.39 g, 0.505 mol), potassium carbonate (276.42 g, 2 mol), and potassium iodide (5.4 g) in DMF (1 L) was stirred and heated at 100-110° C. for 8 hours. About 80% of the solvent was evaporated at reduced pressure, the residue was diluted with dichloromethane (1 L) and washed with brine (3×300 mL) and dried (Na2SO4). Solvent was evaporated from the dichloromethane solution and the residue was treated with isopropanol (400 mL) and cooled. The pale yellow crystalline product formed was filtered, washed with ice-cold isopropanol and dried (168.6 g, 90%); M.p. 96-98° C.

Workup

  1. customAbout 80% of the solvent was evaporated at reduced pressure
  2. additionthe residue was diluted with dichloromethane (1 L)
  3. washwashed with brine (3×300 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated from the dichloromethane solution
  6. additionthe residue was treated with isopropanol (400 mL)
  7. temperaturecooled
  8. customThe pale yellow crystalline product formed
  9. filtrationwas filtered
  10. washwashed with ice-cold isopropanol
  11. customdried (168.6 g, 90%)

Sources & evidence

ORD record
ord-bc376ece06d84dd783743e7420815095
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Linked notes

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