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

HRID 1011623Notes

Reaction equation

HRID 1011623 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:23]([CH3:25])[CH3:24])[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[CH2:13][CH2:14][CH3:15].F[C:27]([F:33])(F)S(O)(=O)=O.[OH-].[Na+]>ClCCl>[CH2:12]([C:16]1([N:23]([CH3:25])[CH3:24])[CH2:21][CH2:20][C:19]([C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH3:11])=[CH:3][C:27]([F:33])=[CH:10][CH:9]=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

6

Reactant 4

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 223515035-Fluoro-3-methyl-1H-indoleHCID 57475098HCID 57475098, compound

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

Procedure

5-fluoro-3-methyl indole (596 mg, 4 mmol) together with 4-butyl-4-(dimethylamino)-cyclohexanone (788 mg, 4 mmol, synthesis cf. WO2008009415, ketone unit Ket-4) was dissolved in dichloromethane (30 ml) and mixed with trifluoromethane sulphonic acid (400 μl, 4.6 mmol). The batch was stirred for 24 h at RT. For work up the reaction mixture was mixed with 2N NaOH (30 ml) and stirred for 20 min at RT. After separation of the organic phase the aqueous phase was extracted with dichloromethane (3×15 ml). The combined organic extracts were dried over Na2SO4 and then concentrated to low volume. The raw product obtained (1.4 g) was purified by column chromatography [silica gel 60 (50 g); ethyl acetate (500 ml)].

Workup

  1. stirringstirred for 20 min at RT
  2. customAfter separation of the organic phase the aqueous phase
  3. extractionwas extracted with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-43ab929d60a9407b913402be9632b63b
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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