Sodium Iodide → HCID 21403006, compound

HRID 1730500Notes

Reaction equation

HRID 1730500 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].[CH3:14][C:15]([OH:29])([CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)CC(=O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:26]2[CH2:27][CH2:28][CH:23]([C:15]([OH:29])([CH3:14])[C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH2:24][CH2:25]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 11356514HCID 11356514, compound

Product 1

HCID 21403006HCID 21403006, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.7 g of 4-chloro-4'-fluorobutyrophenone, 2.5 g of α-methyl-α-(4-piperidyl)-p-fluorobenzyl alcohol, 8 g of sodium carbonate, a crystal of sodium iodide and 30 ml of 4-methyl-2-pentanone is stirred and refluxed for 72 hours. The reaction mixture is worked up in the usual manner as described in the previous Examples. The product is isolated as described above and recrystallized from isopropanol to afford the 4'-fluoro-4-[4-(α-hydroxy-α-methyl-p-fluorobenzyl)-piperidino]-butyrophenone, melting at 116°-118°.

Workup

  1. temperaturerefluxed for 72 hours
  2. customThe product is isolated
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-9efb5ffc02984c039e44636eeca7fa66
Source dataset
uspto-grants-1976_11
Patent number
US03992546

Reaction notes

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