Hydrochloric Acid → HCID 57439855, compound

HRID 902973Notes

Reaction equation

HRID 902973 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][N:26]([CH3:29])[CH2:25][CH2:24]5)=[CH:16][CH:17]=4)[C:12](=[O:30])[C:11]=3[CH:10]=2)[CH2:4][CH2:3]1.[ClH:31].O1CCOCC1>C(OCC)(=O)C.C(O)C>[ClH:31].[ClH:31].[CH3:29][N:26]1[CH2:27][CH2:28][CH:23]([O:22][C:15]2[CH:16]=[CH:17][C:18]3[C:19]4[C:11](=[CH:10][C:9]([O:8][CH:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)=[CH:21][CH:20]=4)[C:12](=[O:30])[C:13]=3[CH:14]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57392852HCID 57392852, compound

Product 1

HCID 57439855HCID 57439855, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,7-bis-(1-methylpiperidin-4-yloxy)-fluoren-9-one (110 mg, 0.27 mmol; Example 24A) in ethyl acetate (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 (74 mg, 0.155 mmol, 57% yield): 1H NMR (300 MHz, CD3OD) δ ppm 1.93-2.36 (m, 8H), 2.92 (s, 6H), 3.10-3.29 (m, 4H), 3.32-3.51 (m, 4H), 4.57-4.78 (m, 2H), 7.10-7.29 (m, 4H), 7.50 (d, J=8 Hz, 2H); MS (DCl/NH3) m/z 407 (M+H)+; Anal. C25H30N2O3.2HCl.0.1H2O: C, H, N.

Workup

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

Sources & evidence

ORD record
ord-1b3473f97da74c20ad49fb20dde960a0
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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