Triethylamine → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dione

HRID 366522Notes

Reaction equation

HRID 366522 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[CH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.I[C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][C:30](=[O:35])[C:29]2=[O:36]>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[C:17][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][C:30](=[O:35])[C:29]3=[O:36])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 886955-IodoisatinHCID 106093551-(3-Butynyl)-4-benzylpiperidine

Product 1

HCID 107618245-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dioneYield 31.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-benzyl-1-(3-butynyl)piperidine (904 mg, 4 mmol), Et3N (4 mL), CuI (76 mg, 0.4 mmol) and Pd(PPh3)2Cl2 (41 mg, 0.1 mmol) in DMF (10 mL) is stirred at room temperature under N2 for 30 min. 5-Iodoisatin (546 mg, 2 mmol) is added and stirring continued overnight. The mixture is evaporated and the residue purified by medium-pressure column chromatography on silica gel eluting with 50% EtOAc/hexanes (+1% Et3N) to give an orange solid (238 mg). The solid is recrystallized from hot 90:10 isopropanol:water to give the title compound as orange crystals (152 mg): mp 140-141° C.

Workup

  1. stirringstirring continued overnight
  2. customThe mixture is evaporated
  3. customthe residue purified by medium-pressure column chromatography on silica gel eluting with 50% EtOAc/hexanes (+1% Et3N)

Sources & evidence

ORD record
ord-c2c039b9ce6d46a39ab20c8178c752b5
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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