Trifluoromethanesulfonic acid → 1-butyl-4,4-bis(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

HRID 1011643Notes

Reaction equation

HRID 1011643 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:11].[CH2:12]([C:16]1([N:44]([CH3:46])[CH3:45])[CH2:21][CH2:20][C:19]([C:22]2[NH:23][C:24]3[C:29]([C:30]=2[CH2:31]CN2C(=O)C4C(=CC=CC=4)C2=O)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH2:17]1)[CH2:13][CH2:14][CH3:15].[F:47]C(F)(F)S(O)(=O)=O>ClCCl>[CH2:12]([C:16]1([N:44]([CH3:46])[CH3:45])[CH2:21][CH2:20][C:19]([C:22]2[NH:23][C:24]3[C:29]([C:30]=2[CH3:31])=[CH:28][C:27]([F:47])=[CH:26][CH:25]=3)([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:11])=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:18][CH2:17]1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 223515035-Fluoro-3-methyl-1H-indoleHCID 669113532-(2-(2-(4-butyl-4-dimethylaminocyclohex-1-enyl)-1H-indol-3-yl)-ethyl)isoindol-1,3-dione

Product 1

HCID 445128401-butyl-4,4-bis(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

5-fluoroskatole (670 mg, 4.49 mmol) together with 2-(2-(2-(4-butyl-4-dimethylaminocyclohex-1-enyl)-1H-indol-3-yl)-ethyl)isoindol-1,3-dione (700 mg, 1.49 mmol) was dissolved in abs. dichloromethane (5 ml) and mixed with trifluoromethane sulphonic acid (0.175 ml, 1.974 mmol). The batch was stirred for 10 d at 24° C. The precipitated light beige-coloured solid was separated by filtration and washed with dichloromethane (3×0.5 ml). The solid (1031 mg) was stirred for 10 min with 1N sodium hydroxide solution (20 ml) and dichloromethane (20 ml). The phases were separated. The aqueous phase was extracted with dichloromethane (2×20 ml). The combined organic extracts were dried over Na2SO4 and then concentrated to low volume. The product was purified by column chromatography.

Workup

  1. customThe precipitated light beige-coloured solid was separated by filtration
  2. washwashed with dichloromethane (3×0.5 ml)
  3. stirringThe solid (1031 mg) was stirred for 10 min with 1N sodium hydroxide solution (20 ml) and dichloromethane (20 ml)
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with dichloromethane (2×20 ml)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated to low volume
  8. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-4951ba1ee2144f4fbff030f76b7dc3a1
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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