3-(2-(4-Pyridyl)ethyl)indole → 1-benzyl-N,N-dimethyl-4,4-bis(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine

HRID 1011624Notes

Reaction equation

HRID 1011624 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:3][CH:2]=1.[CH2:18]([C:25]1([N:32]([CH3:34])[CH3:33])[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.FC(F)(F)S(O)(=O)=O>ClCCl>[CH2:18]([C:25]1([N:32]([CH3:34])[CH3:33])[CH2:30][CH2:29][C:28]([C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 279343-(2-(4-Pyridyl)ethyl)indoleHCID 62406Trifluoromethanesulfonic acidHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 445175721-benzyl-N,N-dimethyl-4,4-bis(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-pyridin-4-ylethyl)-1H-indole (667 mg, 3 mmol, synthesis cf. WO2008009415, indole unit Ind-14) together with 4-benzyl-4-(dimethylamino)cyclohexanone (652 mg, 3 mmol, synthesis cf. WO2008009415, ketone unit Ket-3) was dissolved in abs. dichloromethane (45 ml) and mixed with trifluoromethane sulphonic acid (0.553 ml, 6.3 mmol). The batch was stirred for 67 h at RT, and a brown oil separated out. For work up the reaction solution was mixed with 1N NaOH (10 ml) and THF (10 ml). The mixture was stirred a further 60 min. After separation of the phases the aqueous phase was extracted with dichloromethane (3×10 ml). The combined organic extracts were dried over Na2SO4 and then concentrated to low volume. The raw product obtained (1.22 g) was purified by column chromatography [silica gel 60 (100 g); ethyl acetate/methanol (10:1, 1100 ml), ethyl acetate/methanol (2:1, 500 ml) ethyl acetate/methanol (1:2, 750 ml)].

Workup

  1. customa brown oil separated out
  2. additionFor work up the reaction solution was mixed with 1N NaOH (10 ml) and THF (10 ml)
  3. stirringThe mixture was stirred a further 60 min
  4. customAfter separation of the phases the aqueous phase
  5. extractionwas extracted with dichloromethane (3×10 ml)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-81252ca81d944f50ad8182130792ea9c
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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