Potassium Iodide → 1-[3-(4-Chlorophenoxy)propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanol

HRID 1709879Notes

Reaction equation

HRID 1709879 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33]Cl)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][N:13]2[CH2:12][CH2:11][CH:10]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:9])[CH2:15][CH2:14]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 12685610HCID 12685610, compound

Product 1

HCID 144070841-[3-(4-Chlorophenoxy)propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.0 g (0.01 mole) of [α,α-bis(p-fluorophenyl)]4-piperidinemethanol, 2.0 g (0.01 mole) of 1-chloro-4-(3-chloropropoxy)benzene, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol was heated at reflux for 20 hr to give, after working up as in Example 1 (recrystallizing the free base from isopropyl alcohol), 1.7 g (36%) of white solid, m.p. 92°-93° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. customto give
  4. customrecrystallizing the free base from isopropyl alcohol), 1.7 g (36%) of white solid, m.p. 92°-93° C.

Sources & evidence

ORD record
ord-52f29875c41249a0975bd2e69259d96e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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