Toluene → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

HRID 366517Notes

Reaction equation

HRID 366517 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.BrC1[CH:22]=[C:23]2C(=CC=1)[NH:26][CH:25]=[CH:24]2.[C:30]1(S(Cl)(=O)=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:40]1([CH3:46])[CH:45]=[CH:44]C=[CH:42][CH:41]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].O>[CH2:46]([CH:40]1[CH2:41][CH2:42][N:26]([CH2:25][CH2:24][C:23]#[C:22][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[NH:10][CH:11]=[CH:12]3)[CH2:44][CH2:45]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 7369Benzenesulfonyl chlorideHCID 249055-BromoindoleHCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indole

Product 1

HCID 106410735-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-Benzenesulfonyl-5-bromoindole. A mixture of 5-bromoindole (5 g, 25.5 mmol) and tetra-n-butylammonium hydrogen sulfate (866 mg, 2.55 mmol) in 50% NaOH (50 mL) and toluene (200 mL) is stirred at room temperature for 5 min. Benzenesulfonyl chloride (3.57 mL, 28 mmol) is added and the mixture stirred for 1 hr. The mixture is diluted with water (500 mL) and extracted with EtOAc (3×100 mL). The extracts are washed with brine (250 mL), dried over MgSO4, filtered and evaporated to a yellow oil. The oil is purified by medium-pressure column chromatography on silica gel eluting with 10% EtOAc/hexanes to give the title compound as a white solid (7.81 g).

Workup

  1. stirringthe mixture stirred for 1 hr
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe extracts are washed with brine (250 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. customThe oil is purified by medium-pressure column chromatography on silica gel eluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-fd3c74e9053c4d6b856d6c9a3df5f433
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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