2-Bromomethylnaphthalene → HCID 14280704, compound

HRID 1614614Notes

Reaction equation

HRID 1614614 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.Br[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1.C(=O)(O)[O-].[Na+]>C(O)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 516892Sodium BicarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 14280704HCID 14280704, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 15.1 g (0.062 mol) 4-(4-fluorobenzoyl)piperidine hydrochloride, 13.77 g (0.062 mol) of 2-(bromomethyl)naphthalene and 13.6 g (0.16 mol) of sodium bicarbonate in 500 mL of absolute ethanol was stirred at room temperature for 16 hr. The solvent was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo. The residue was recrystallized from 400 mL of methanol to give 11.81 g (54.9%) of white crystalline solid, mp 131°-134° C. The filtrate was subjected to flash chromatography (silica gel, gradiently eluted with CH3OH/CH2Cl2) to give an additional 2.84 g (13.2%) of the title compound.

Workup

  1. customThe solvent was partitioned between CH2Cl2 and dilute NaOH
  2. dry with materialThe CH2Cl2 solution was dried (Na2SO4)
  3. customthe solvent was removed in vacuo
  4. customThe residue was recrystallized from 400 mL of methanol

Sources & evidence

ORD record
ord-d56650669cba45b2b56a0fd2a9eb79e4
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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