p-Toluenesulfonic acid monohydrate → HCID 86601087, compound

HRID 553042Notes

Reaction equation

HRID 553042 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([N:21]5[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]5)=[CH:15][CH:16]=4)[C:11](=[O:28])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.O.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1>CCO.CCOC(C)=O.CCO>[C:30]1([CH3:40])[CH:31]=[CH:32][C:33]([S:36]([OH:39])(=[O:37])=[O:38])=[CH:34][CH:35]=1.[C:30]1([CH3:40])[CH:31]=[CH:32][C:33]([S:36]([OH:39])(=[O:37])=[O:38])=[CH:34][CH:35]=1.[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:20]=[CH:19][C:18]3[C:17]4[C:12](=[CH:13][C:14]([N:21]5[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]5)=[CH:15][CH:16]=4)[C:11](=[O:28])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57403295HCID 57403295, compound

Product 1

HCID 86601087HCID 86601087, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 2,7-bis-(4-methylpiperazin-1-yl)-fluoren-9-one from Example 27A (120 mg, 0.319 mmol) in EtOH-EtOAc (2 mL) was added a solution of p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol; Aldrich) in EtOH (2 mL). The mixture was stirred overnight and the purple precipitate was collected by filtration to afford the title compound (102 mg, 0.14 mmol; 89% yield based on p-toluenesulfonic acid monohydrate): 1H NMR (300 MHz, CD3OD) δ ppm 7.70 (d, J=8 Hz, 4H), 7.45 (d, J=8 Hz, 2H), 7.19-7.27 (m, 6H), 7.13 (dd, J=8, 2 Hz, 2H), 2.96 (s, 6H), 2.35 (s, 6H); MS (DCI/NH3) m/z 377 (M+H)+; Anal. C23H28N4O.2C7H8O3S.0.1H2O: C, H, N.

Workup

  1. filtrationthe purple precipitate was collected by filtration

Sources & evidence

ORD record
ord-bd4824e4378a4c00b1ea324806ed48e7
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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