Hydrochloric Acid → HCID 18946764, compound

HRID 1769195Notes

Reaction equation

HRID 1769195 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][CH:5]=1.I[CH2:21][CH2:22][CH2:23][CH3:24].Cl>CN(C=O)C>[CH2:21]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 107795362-[(4-Bromophenyl)methyl]-1H-indole

Product 1

HCID 18946764HCID 18946764, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of sodium hydride (0.32 g) in DMF (50 ml) was cooled in an ice bath. A solution of 2-(p-bromophenylmethyl)indole (2.0 g), prepared, e.g., as described in Preparation 3, in DMF, was added, and the mixture stirred for 10 minutes. 1-Iodobutane (0.9 ml) in DMF was added dropwise, and the mixture stirred for 30 minutes. It was then poured into cold dilute HCl and extracted with ether. The extract was washed three times with cold water, dried over magnesium sulphate, and the solvent evaporated to afford an orange-red oil, 1-(n-butyl)-2-(p-bromophenylmethyl)indole (2.5 g), a compound of Formula (9).

Workup

  1. temperaturewas cooled in an ice bath
  2. additionwas added
  3. stirringthe mixture stirred for 30 minutes
  4. extractionextracted with ether
  5. washThe extract was washed three times with cold water
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-e1349fe90c6a40b0b918910dd6e8e4d6
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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