Potassium Carbonate → HCID 69737831, compound

HRID 896552Notes

Reaction equation

HRID 896552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:4][CH:3]=1.Cl.Cl.[CH2:23]([O:25][C:26]([C@H:28]1[C@H:33]([N:34]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:35])[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:27])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:23]([O:25][C:26]([C@H:28]1[C@H:33]([N:34]([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:35])[CH2:32][CH2:31][N:30]([CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:29]1)=[O:27])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17390106Benzeneethanol, 4-fluoro-, 1-(4-methylbenzenesulfonate)HCID 69736404trans-4-(Benzyl-methyl-amino)-piperidine-3-carboxylic Acid Ethyl Ester Dihydrochloride

Product 1

HCID 69737831HCID 69737831, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-(4-fluorophenyl)-ethyl ester (containing 10% by weight of 2-(4-fluorophenyl)ethanol; 206 mg, 630 μmol), trans-4-(benzyl-methyl-amino)-piperidine-3-carboxylic acid ethyl ester dihydrochloride (220 mg, 630 μmol) and potassium carbonate (261 mg, 1.9 mmol) in acetonitrile (6 mL) was heated at reflux for 17 hours. The mixture was cooled and filtered, the solid was washed with acetonitrile, and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography, eluting with 20%, then 30% ethyl acetate in hexane, to provide an oil (164 mg, 65%). 1H NMR (300 MHz, CDCl3) δ7.28 (m, 5H), 7.16 (m, 2H), 6.98 (t, J=9 Hz, 2H), 4.20 (m, 2H), 3.75 (d, J=13 Hz, 1H), 3.48 (d, J=13 Hz, 1H), 3.14 (m, 2H), 2.88 (m, 2H), 2.80 (m, 2H), 2.62 (m, 2H), 2.29 (m, 1H), 2.20 (s, 3H), 1.87 (m, 1H), 1.70 (m, 2H), 1.28 (t, J=7 Hz, 3H).

Workup

  1. temperatureat reflux for 17 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid was washed with acetonitrile
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20%

Sources & evidence

ORD record
ord-f0f4e96f62544bea997f52938f7f0b21
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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