Hydrochloric Acid → 2-(1-(4-fluorophenethyl)-5-chloro-1H-indol-3-yl)-N-methylethanamine

HRID 1775912Notes

Reaction equation

[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)N)=[CH:4][CH:3]=1.Cl.O1CCOCC1.C(O[CH:29](OCC)[CH2:30][CH2:31][CH2:32][NH:33][CH3:34])C.Cl>C(OCC)(=O)C.C(O)C.O>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[C:30]([CH2:31][CH2:32][NH:33][CH3:34])=[CH:29]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The title compound was prepared by General Method 3. 1-(4-fluorophenethyl)-1-(4-chlorophenyl)hydrazine (500 mg) was converted into its hydrochloride salt by dissolving in ethyl acetate and treatment of dioxane-HCl. The salt was dissolved in ethanol/water (1/1; 4 mL)) and was heated to 60° C. 4,4-diethoxy-N-methylbutan-1-amine (0.35 g) was added and the temperature was raised to 70-80° C. 28% aqueous HCl (0.24 mL) was added and the heating was continued for 40 min. Additional amount of 4,4-diethoxy-N-methylbutan-1-amine (0.3 g) and % aqueous HCl (0.3 mL) was added and heating was continued for additional 3 h after which the reaction mixture was cooled and stirred at 25° C. for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 7/3/1) to obtain 600 mg of product.

Workup

temperaturethe temperature was raised to 70-80° C
temperatureheating
waitwas continued for additional 3 h
temperatureafter which the reaction mixture was cooled
concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (eluent EtOAc/EtOH/NH3: 7/3/1)

Sources & evidence

ORD record: ord-e4175597cdc8488fb29935eac06ab26a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260429B2

Reaction notes

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