Water → HCID 70096326, compound

HRID 1459430Notes

Reaction equation

HRID 1459430 reaction equation
N1C=CC([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=CC=1.[Li+].[OH-].O>C1COCC1>[N:7]1[CH:12]=[CH:17][C:16]([O:15][C:13]([CH:10]2[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]2)=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 9899468Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate

Product 1

HCID 70096326HCID 70096326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 33-1 (10 g, 42.7 mmol) in THF (50 mL) was treated with 1N LiOH (47 mL, 47.0 mmol) and water (50 mL). The resulting solution was stirred at ambient temperature for 12 h. The solution was concentrated and the aqueous residue was cooled to 0° C., then adjusted to pH=6 with 1N HCl. The resulting solid was collected by filtration and dried in vacuo to afford 33-2 as a white solid. 1H NMR (D2O) δ 7.95 (d, J=6.8 Hz, 2HO, 6.73 (d, J=6.8 Hz, 2h), 3.76 (d, J=12.8 Hz, 2HO, 2.81 (m, 2H), 2.20 (m, 1H), 1.85 (d, J=12.9 Hz, 2H), 1.55 (m, 2H). ##STR165## Ethyl 4-(Pyridyl)(piperidin-4-yl)-carbonylamino-3-methylphenoxyacetate (33-3)

Workup

  1. concentrationThe solution was concentrated
  2. temperaturethe aqueous residue was cooled to 0° C.
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b09e636be20f4c8c921e443047b491c3
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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