Tetrabutylammonium Fluoride → 3-(4-piperidyl)-1H-indole

HRID 737014Notes

Reaction equation

HRID 737014 reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[N:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([Si](C(C)C)(C(C)C)C(C)C)[CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1.CCOC(C)=O>[N:19]1([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589749863-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 870923-(4-piperidyl)-1H-indoleYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add nBu4NF (1.0M in THF, 3.2 mL, 3.2 mmol) to a solution of 3-piperidin-1-yl-1-triisopropylsilanyl-1H-indole (835 mg, 2.34 mmol) in THF (10 mL). Stir the red solution at RT for 1 h, then dilute with EtOAc (40 mL) and wash with satd NaHCO3 (20 mL). Dry, filter, and concentrate the organic solution then purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 40% EtOAc/hexanes. Obtain the title compound (347 mg, 74%) as a grey solid. MS (ES+) 201.1 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 7.65 (d, 1H, J=8.1), 7.59 (br s, 1H), 7.29 (d, 1H, J=8.4), 7.16 (t, 1H, J=7.5), 7.06 (t, 1H, J=7.9), 6.70 (s, 1H), 3.03 (m, 4H), 1.80 (m, 4H), 1.59 (m, 2H).

Workup

  1. washwash with satd NaHCO3 (20 mL)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic solution
  5. customthen purify the crude material by flash chromatography

Sources & evidence

ORD record
ord-a3c31f2f74d54c90a5f671857292e8e9
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…