1-Bromoheptane → 5-Benzyloxy-1-heptylindole

HRID 1821960Notes

Reaction equation

HRID 1821960 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 123691-BromoheptaneHCID 146245-BenzyloxyindoleHCID 14797Potassium Hydroxide

Product 1

HCID 688426665-Benzyloxy-1-heptylindole

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

0.22 g (4.45 mmol) pulverized, 88% potassium hydroxide, 0.5 g (2.24 mmol) 5-benzyloxyindole and 0.07 g (0.22 mmol) tetrabutylammoniumbromide are weighed out in the given order and mixed with 1.41 ml (8.96 mmol) 1-bromoheptane with vigorous stirring. The mixture is stirred at room temperature overnight. Having added 30 ml water, three extractions using diethyl ether are carried out. The organic phase is washed three times with saturated NaCl solution, dried on sodium sulfate and the solvent is removed in vacuo. The residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 95:5). The product accrues as an oil.

Workup

  1. additionHaving added
  2. extraction30 ml water, three extractions
  3. washThe organic phase is washed three times with saturated NaCl solution
  4. customdried on sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-149482f5fe0e4210882e07c51aa50255
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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