Sodium hydride → HCID 54568120, compound

HRID 1721609Notes

Reaction equation

HRID 1721609 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:20])[C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:7]=1[OH:19].[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28](Cl)=[O:29])[CH2:24][CH2:23]1>C1C=CC=CC=1>[CH3:3][O:4][C:5]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:7]=1[O:19][C:28]([N:25]1[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]1)=[O:29])=[O:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 540768352-Hydroxy-5-phenoxybenzoic acid methyl ester

Product 1

HCID 54568120HCID 54568120, compoundYield 111.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Sodium hydride (0.38 g, 9.93 mmol of a 60% oil dispersion) was added in portions under a nitrogen atmosphere to a solution of 2-hydroxy-5-phenoxybenzoic acid methyl ester (2.0 g, 8.19 mmol) in 30 ml of benzene. The reaction was stirred at room temperature for 30 minutes. 4-Methyl-1-piperidinecarbonyl chloride (1.46 g, 9.03 mmol) was then added and the reaction refluxed for 3.5 hours. The reaction mixture was washed with 1N HCl, dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give 3.38 g of a clear oil. Purification of this oil on 300 g of silica gel (230-400 mesh) using hexane-methylene chloride as the eluent gave 2.71 g of a white crystalline solid. Recrystallization of this solid from diisopropyl ether-hexane then gave the title compound as a white crystalline solid (2.02 g, 67%), mp 67°-69C.

Workup

  1. temperaturethe reaction refluxed for 3.5 hours
  2. washThe reaction mixture was washed with 1N HCl
  3. dry with materialdried (anhydrous MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-41b7e09072134fed83e46eb9e69eaa4b
Source dataset
uspto-grants-1996_04
Patent number
US05512565

Reaction notes

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