Potassium Iodide → 5-[4-(alpha-Hydroxy-alpha-phenylbenzyl)piperidino]-4'-piperidinovalerophenone

HRID 267981Notes

Reaction equation

HRID 267981 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:33])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:32])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.Cl.FC1C=CC(C(=O)CCCC[N:47]2[CH2:52][CH2:51][CH:50](C(O)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:49][CH2:48]2)=CC=1.[I-].[K+]>N1CCCCC1>[OH:32][C:19]([CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)=[CH:3][CH:4]=2)=[O:33])[CH2:14][CH2:15]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 215529524'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone hydrochlorideHCID 215529534'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone

Product 1

HCID 215529835-[4-(alpha-Hydroxy-alpha-phenylbenzyl)piperidino]-4'-piperidinovalerophenone

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A mixture of 15.6 g (0.35 mole) of 4'-fluoro-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone, the free base of the compound of Example 2, and a small amount of potassium iodide in 100 ml of piperidine is refluxed for about 22 hours. The unreacted piperidine is removed under vacuum, and the remaining residue is triturated with water. The water is decanted and the residue is dissolved in methanol and then added to a large amount of water. The resulting precipitate is dissolved in a large volume of ether, dried over magnesium sulfate, and filtered. The filtrate is concentrated and cooled yielding a product which is recrystallized from ether to give 5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]-4'-piperidinovalerophenone.

Workup

  1. customThe unreacted piperidine is removed under vacuum
  2. customthe remaining residue is triturated with water
  3. customThe water is decanted
  4. dissolutionthe residue is dissolved in methanol
  5. additionadded to a large amount of water
  6. dissolutionThe resulting precipitate is dissolved in a large volume of ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated
  10. temperaturecooled
  11. customyielding a product which
  12. customis recrystallized from ether

Sources & evidence

ORD record
ord-d6ccedfca1f04e7cbaad2ab37528ac23
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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