Potassium Carbonate → 5-[2-[4-[(4-Fluorophenyl)methyl]-1-piperidinyl]ethoxy]-1,3-dihydro-2H-indol-2-one

HRID 1955257Notes

Reaction equation

HRID 1955257 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:11][CH2:12][CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:8]=2)[NH:3]1.[F:25][C:26]1[CH:38]=[CH:37][C:29]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][CH:31]2[CH2:32][CH2:33][N:34]([CH2:13][CH2:12][O:11][C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:10]4)[CH2:35][CH2:36]2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 54323087HCID 54323087, compound

Product 1

HCID 232942775-[2-[4-[(4-Fluorophenyl)methyl]-1-piperidinyl]ethoxy]-1,3-dihydro-2H-indol-2-oneYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of toluene-4-sulfonic acid 2-(2-oxo-2,3-dihydro-1H-indol-5-yloxy)-ethyl ester (0.77 g, 2.22 mmol), 4-(4-fluorobenzyl)piperidine (1.1 g, 5.63 mmol), and potassium carbonate (2.2 g, 15.92 mmol) in acetonitrile (75 ml) was refluxed overnight under argon. The reaction mixture was cooled to room temperature and the solid was filtered off and washed with THF (3×20 ml). The filtrate was evaporated, and the solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate to give the title compound (0.62 g, 76%) as a solid, mp 149-150° C. Analysis calculated for C22H25FN2O2 ·0.14H2O: C, 71.21; H, 6.87; N, 7.55; F, 5.12. Found: C, 71.21; H, 6.68; N, 7.49; F, 5.26.

Workup

  1. temperaturewas refluxed overnight under argon
  2. filtrationthe solid was filtered off
  3. washwashed with THF (3×20 ml)
  4. customThe filtrate was evaporated
  5. customthe solid chromatographed on silica gel eluting with 35% methanol/ethyl acetate

Sources & evidence

ORD record
ord-864d5909d54c406ea7497077cc0e6f41
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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