Ethylene Glycol → HCID 59075508, compound

HRID 1356365Notes

Reaction equation

C([N:9]1[CH2:22][CH2:21][CH:20]2[CH:12]([NH:13][C:14]3[CH:15]=[C:16]([Cl:24])[C:17]([Cl:23])=[CH:18][C:19]=32)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].C(O)CO>O>[Cl:24][C:16]1[C:17]([Cl:23])=[CH:18][C:19]2[C@@H:20]3[CH2:21][CH2:22][NH:9][CH2:10][CH2:11][C@H:12]3[NH:13][C:14]=2[CH:15]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 3-benzoyl-8,9-dichloro-1,2,3,4,5,5a,6,10b-octahydroazepino[4,5-b]indole (0.20 g, 0.55), potassium hydroxide (1.0 g, 17.8 mmol), and ethylene glycol (5 mL) was heated to 170° C. Upon the disappearance of starting material, the reaction was cooled to room temperature, diluted with H2O, and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography and prep HPLC to give the title compound (31 mg, 22%) as a tan solid. 1H NMR (d-MeOH) δ 8.54, 7.02, 6.63, 3.73, 3.08-2.88, 2.40, 2.17, 1.81, 1.65; IR (drift) 2934, 2916, 2866, 2850, 2831, 1627, 1608, 1569, 1481, 1466, 1372, 1365, 953, 775, 662 cm−1; HRMS (FAB) calcd for C12H14Cl2N2+H 257.0612, found 257.0619.

Workup

temperatureUpon the disappearance of starting material, the reaction was cooled to room temperature
extractionextracted with CH2Cl2
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
customdecanted
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography and prep HPLC

Sources & evidence

ORD record: ord-01e6f5c6bf7847a8a5bba388bb88fa6e
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586421B2

Reaction notes

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