Ethanol → 9-(8-Aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthene-3-carboxylic acid diethylamide

HRID 733389Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide, 8a (3 g, 7.7 mmol) in chloroform (50 mL) were added ethanol (2.25 mL, 38.6 mmol) and trimethylsilyl iodide (5.25 mL, 38.6 mmol). The mixture was stirred at 100° C. for 2 h in a sealed tube. The reaction was allowed to cool to rt and washed with 1 N NaOH, aqueous Na2S2O4, and brine. The organic phase was dried over sodium sulfate, filtered, and concentrated, to yield title compound 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthene-3-carboxylic acid diethylamide, 9a (3.0 g, 0.53 mmol). MS m/z=391.4 (MH+)

Workup

temperatureto cool to rt
washwashed with 1 N NaOH, aqueous Na2S2O4, and brine
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-347a6090a9414b3380375744e7b78a00
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589104B2

Reaction notes

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