Sodium Carbonate → HCID 22935574, compound

HRID 1272286Notes

Reaction equation

HRID 1272286 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[CH3:9][C:10]1([CH3:30])[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:13]2[C:22]([CH3:29])=[C:23]([NH2:28])[C:24]([CH3:27])=[C:25]([CH3:26])[C:12]=2[O:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[ClH:2].[CH3:9][C:10]1([CH3:30])[CH:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[C:13]2[C:22]([CH3:29])=[C:23]([N:28]3[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]3)[C:24]([CH3:27])=[C:25]([CH3:26])[C:12]=2[O:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

Product 1

HCID 22935574HCID 22935574, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Bis(2-chloroethyl)amine hydrochloride (18.7 g, 105 mmol) was added to a suspension of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (29.5 g, 100 mmol) in 1-butanol (300 mL) and the mixture was refluxed for 24 hours under argon atmosphere. The reaction mixture was cooled to room temperature and then sodium carbonate (12.7 g, 120 mmol) was added. The resulting mixture was refluxed for 24 hours and concentrated under reduced pressure. The residue was diluted with water (500 ml) and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified on basic silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain a free base of the title compound as an oil residue.

Workup

  1. temperaturethe mixture was refluxed for 24 hours under argon atmosphere
  2. temperatureThe resulting mixture was refluxed for 24 hours
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water (500 ml)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified on basic silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-30d6870e206d4b43a63557e1ce57eb06
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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