Water → N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]acetamide

HRID 2268477Notes

Reaction equation

HRID 2268477 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:7]2.C(=O)([O-])[O-].[K+].[K+].O.[C:34](Cl)(=[O:36])[CH3:35]>C(OCC)(=O)C>[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:34](=[O:36])[CH3:35])[CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 18348528HCID 18348528, compound

Product 1

HCID 18348615N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 8-(4,5,6,7-tetramethoxyindan-2-yl)octylamine (878 mg), potassiumcarbonate (2.54 g),water (16 ml), and ethyl acetate (16 ml) was dropwise added acetyl chloride (0.341 ml) with cooling with ice. After being stirred for 15 min, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate) and then with recrystallization (hexane-ethyl acetate) to give the entitled compound (0.830 g) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customwith recrystallization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3f2a4129b7954ec48d69da6ee93dffdc
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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