2-Bromo-2'-acetonaphthone → 2-[4-(alpha-Hydroxy-p-fluorobenzyl)piperidinyl]-2'-acetonaphthone

HRID 1649775Notes

Reaction equation

HRID 1649775 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[OH:15][CH:16]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(O)C>[OH:15][CH:16]([CH:24]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=2)=[O:4])[CH2:26][CH2:25]1)[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 691792-Bromo-2'-acetonaphthoneHCID 516892Sodium BicarbonateHCID 4778266(4-Fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 142807442-[4-(alpha-Hydroxy-p-fluorobenzyl)piperidinyl]-2'-acetonaphthone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.4 g of 2-bromo-2'-acetonaphthone, 4.6 of 4-(α-hydroxy-p-fluorobenzyl)piperidine and 10 g of sodium hydrogencarbonate were refluxed in ethanol solvent for 2.5 h. After completion of the reaction, the product was treated by an ordinary process. The obtained oily product was purified according to silica gel column chromatography to obtain 5 g of 2-[4-(α-hydroxy-p-fluorobenzyl)piperidinyl]-2'-acetonaphthone; 1 g of this product was stirred together with 1.0 g of acetic anhydride and 0.1 g of dimethylaminopyridine in pyridine solvent at room temperature for 5 h. After completion of the reaction, the oily product was purified according to silica gel column chromatography and converted into its hydrochloride, which was recrystallized from ethyl acetate and methanol.

Workup

  1. customAfter completion of the reaction
  2. additionthe product was treated by an ordinary process
  3. customThe obtained oily product was purified

Sources & evidence

ORD record
ord-5a359870201f44229f092665f1d936b3
Source dataset
uspto-grants-1990_05
Patent number
US04921863

Reaction notes

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