Piperidine → HCID 10777660, compound

HRID 2121207Notes

Reaction equation

HRID 2121207 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].Cl.Cl[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].N1CCCCC1>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][C:5]=1[OH:11]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 10777660HCID 10777660, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture in acetone (40 mL) and water (10 mL) of 2,4-dihydroxybenzoic acid methyl ester (1.19 g, 7.08 mmol), prepared as in Example 240A, 3-chloromethylpyridine hydrochloride (2.32 g, 14.2 mmol) and potassium carbonate (2.44 g, 21.2 mmol) was stirred at reflux for 24 hours, then acetone (10 mL) and piperidine (1 g) were added and reflux was continued for 12 hours. The reaction mixture was cooled to ambient temperature, poured into water, and extracted with ethyl acetate (3×). The combined organic extracts were washed with aqueous sodium hydroxide and water, dried, filtered and concentrated in vacuo. The residue was recrystallized from aqueous ethanol to give 4-(3-pyridylmethyloxy)-2-hydroxybenzoic acid methyl ester (0.57 g, 31%).

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturereflux
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with aqueous sodium hydroxide and water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3f330f72250e496a8cdf37f1eb304e23
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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