Formaldehyde → HCID 90016046, compound

HRID 1484423Notes

Reaction equation

HRID 1484423 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[CH:5]2.C=O.[CH2:21]([NH:23][CH2:24]C)[CH3:22]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[C:5]2[CH2:24][NH:23][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 49782540HCID 49782540, compound

Product 1

HCID 90016046HCID 90016046, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 5-bromo 1-octyl 1H-indole (2 mmol) in acetic acid (10 ml) was added formaldehyde (0.5 ml) and diethyl amine (4 mmol), reaction was stirred at RT overnight, reaction were monitored by TLC. Reaction was quenched by methylene chloride 20 ml, and 15 ml of water and pH was adjusted to 9 using 1N NaOH solution. Added more methylene chloride and organic layer was washed with water. Combined organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure to obtain the crude residue. The crude material was purified by column chromatography in chloroform and Methanol solvent system to get oily product. Product was confirmed by LC-MS and NMR. Yield 40 to 60%.

Workup

  1. customreaction
  2. customReaction
  3. customwas quenched by methylene chloride 20 ml, and 15 ml of water and pH
  4. additionAdded more methylene chloride and organic layer
  5. washwas washed with water
  6. washCombined organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customto obtain the crude residue
  10. customThe crude material was purified by column chromatography in chloroform
  11. customMethanol solvent system to get oily product

Sources & evidence

ORD record
ord-aca4a8f0397f45e6bdfd19b907fd78e2
Source dataset
uspto-grants-2016_08
Patent number
US09422238B2

Reaction notes

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