Hydrochloric Acid → HCID 67163658, compound

HRID 902990Notes

Reaction equation

HRID 902990 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][C:15]([O:22][CH:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)=[CH:16][CH:17]=4)[C:12](=[O:29])[C:11]=3[CH:10]=2)[CH2:4][CH2:3]1.[ClH:30].O1CCOCC1>CCOC(C)=O.C(O)C>[ClH:30].[ClH:30].[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:21]=[CH:20][C:19]3[C:18]4[C:13](=[CH:14][C:15]([O:22][CH:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)=[CH:16][CH:17]=4)[C:12](=[O:29])[C:11]=3[CH:10]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57439209HCID 57439209, compound

Product 1

HCID 67163658HCID 67163658, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1-methylpiperidin-4-yloxy)-7-(piperidin-4-yloxy)-fluoren-9-one (81 mg, 0.21 mmol; Example 24A) in EtOAc (10 mL) containing a few drops of ethanol was added a solution of HCl in dioxane (4 M, 335 μL, 1.34 mmol; Aldrich). After stirring the mixture for 2 h, the solid was collected by filtration and recrystallized from hot EtOH-EtOAc to afford the title compound (50 mg, 0.11 mmol, 51% yield): 1H NMR (300 MHz, CD3OD) δ ppm 1.97-2.11 (m, 3H), 2.11-2.27 (m, 4H), 2.92 (s, 3H), 3.18-3.30 (m, 4H), 3.35-3.47 (m, 4H), 4.72-4.81 (m, 2H), 7.14 (dd, J=8, 2 Hz, 2H), 7.22 (d, J=2 Hz, 2H), 7.50 (d, J=8 Hz, 2H); MS (DCl/NH3) m/z 393 (M+H)+; Anal. C24H28N2O3.2HCl: C, H, N.

Workup

  1. filtrationthe solid was collected by filtration
  2. customrecrystallized from hot EtOH-EtOAc

Sources & evidence

ORD record
ord-558e6ec9a43f4ca8b6e059efd16e55f9
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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