Potassium Iodide → 2-[3-[4-[Bis(4-fluorophenyl)methyl]-1-piperidinyl]propoxy]benzonitrile

HRID 1709895Notes

Reaction equation

HRID 1709895 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[C:29]#[N:30])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 144071832-(3-Chloropropoxy)benzonitrile

Product 1

HCID 144071422-[3-[4-[Bis(4-fluorophenyl)methyl]-1-piperidinyl]propoxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.41 g (0.025 mole) of [4-[bis(4-fluorophenyl)methyl]piperidine, 4.90 g (0.025 mole) of 2-(3-chloropropoxy)benzonitrile, and potassium carbonate, 5.54 g (0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The mixture was concentrated to dryness and the resulting residue was partitioned several times between water and chloroform. The chloroform layer was dried (anhydrous sodium sulfate), filtered, and solvent removed to give a brown oil. The oil was triturated with ethyl ether and placed in a freezer overnight. White crystals were obtained and dried in vacuo overnight at room temperature. A yield of 5.15 g (46.1%) of analytically pure material, m.p. 88.5°-90° C., was obtained.

Workup

  1. temperaturewas heated overnight
  2. concentrationThe mixture was concentrated to dryness
  3. customthe resulting residue was partitioned several times between water and chloroform
  4. dry with materialThe chloroform layer was dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customsolvent removed
  7. customto give a brown oil
  8. customThe oil was triturated with ethyl ether
  9. customWhite crystals were obtained
  10. customdried in vacuo overnight at room temperature
  11. customA yield of 5.15 g (46.1%) of analytically pure material, m.p. 88.5°-90° C., was obtained

Sources & evidence

ORD record
ord-b1ef3332b59c41bb89fed3286c5d3d37
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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