5-Benzyloxy-1-heptylindole → HCID 68839366, compound

HRID 1821961Notes

Reaction equation

HRID 1821961 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:13]=[CH:12]2)C1C=CC=CC=1>CO.ClCCl.[Pd]>[CH2:18]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 1

HCID 688426665-Benzyloxy-1-heptylindole

Product 1

HCID 68839366HCID 68839366, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.5 g (1.55 mmol) 5-benzyloxy-1-heptylindole is dissolved in a Schlenk flask in 10 ml methanol and 4 ml dichloromethane. 0.06 g Pd (10%)/C is added and the mixture is rinsed with nitrogen for 15 minutes. Thereafter, a balloon filled with hydrogen is placed on the Schlenk piston and hydrogenation is carried out at room temperature for 12 h. The batch is filtrated on a frit and the solvent is removed in vacuo. The residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 9:1). The product accrues as an oil.

Workup

  1. washthe mixture is rinsed with nitrogen for 15 minutes
  2. additionThereafter, a balloon filled with hydrogen
  3. filtrationThe batch is filtrated on a frit
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ec2be7085d344be6ad50bab997d434e9
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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