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

HRID 736974Notes

Reaction equation

HRID 736974 reaction equation
N1(C2C3C(=CC=CC=3)NC=2)CCOCC1.[N:16]1([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([Si](C(C)C)(C(C)C)C(C)C)[CH:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[N:16]1([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 125308333-Morpholin-4-yl-1H-indoleHCID 589749863-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 870923-(4-piperidyl)-1H-indoleYield 71.3%

Procedure

Following a method similar to 3-morpholin-4-yl-1H-indole using 3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole (0.30 g, 0.84 mmol) and 1N solution of tetrabutylammonium fluoride (1.30 mL). Purify by flash chromatography using 20 to 50% of EtOAc in hexanes to give the title compound (0.12 g 71%). MS (ES) 201.1 (M+1)+.

Workup

  1. customPurify by flash chromatography

Sources & evidence

ORD record
ord-995f1ba85bb046fda717dae1cd01f769
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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