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

HRID 2198293
Notes
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Reaction equation

HRID 2198293 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 139945474,4-Diethoxy-N-methylbutan-1-amine2×HCID 204431481,4-Dioxane hydrochlorideHCID 668689801-(4-Fluorophenethyl)-1-(4-chlorophenyl)hydrazine

Product 1

HCID 669117692-(1-(4-fluorophenethyl)-5-chloro-1H-indol-3-yl)-N-methylethanamine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 19096565Water ethanolSolvent

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

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

Sources & evidence

ORD record
ord-2342edbac48e435d96aae7254da10843
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338447B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes