Tetrabutylammonium Fluoride → 4-(4-Benzyl-piperazin-1-yl)-1H-indole

HRID 1006416

Reaction equation

HRID 1006416 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[C:13]2[C:8](=[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][N:14]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[CH:7]=[CH:6][NH:5]3)[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 226712611-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole

Product 1

HCID 27285324-(4-Benzyl-piperazin-1-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.2 gram (2.68 mmole) 1-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole in 20 mL tetrahydrofuran was added 3 mL (3 mmole) 1.0 M tetrabutylammonium fluoride in tetrahydrofuran. After 2 hours the solution was concentrated under reduced pressure and the residue was partitioned between 25 mL ethyl ether and 10 mL 10% sodium carbonate. The organic phase was washed with 3×10 mL water, dried (magnesium sulfate), and concentrated. 4-(4-Benzyl-piperazin-1-yl)-1H-indole was isolated as the white hydrochloride salt from ethyl ether, 604 mg, m.p. 233-234° C.

Workup

  1. concentrationAfter 2 hours the solution was concentrated under reduced pressure
  2. customthe residue was partitioned between 25 mL ethyl ether and 10 mL 10% sodium carbonate
  3. washThe organic phase was washed with 3×10 mL water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-26dcf6bbf05a427292e269124172fdfc
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Linked notes

Loading…