Triethylamine → N,N-Dimethyl-4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzamide

HRID 2268487Notes

Reaction equation

HRID 2268487 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][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)[CH2:7]2.Cl.[CH3:32][NH2+:33][CH3:34].O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH3:32][N:33]([CH3:34])[C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([O:21][CH2:20][CH2:19][CH2:18][CH:6]2[CH2:5][C:4]3[C:8](=[C:9]([O:16][CH3:17])[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]=3[O:2][CH3:1])[CH2:7]2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 183485514-[3-(4,5,6,7-Tetramethoxyindan-2-yl)propoxy]benzoic acidHCID 18348643Dimethylammonium hydrochloride

Product 1

HCID 18348568N,N-Dimethyl-4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 4-[3-(4,5,6,7-tetramethoxyindan-2-yl)propoxy]benzoic acid (2.00 g), dimethylammonium hydrochloride (783 mg), 1-ethyl-3-(3-dimethylaminopropyl)carboduimide hydrochloride (1.84 g), 1-hydroxybenzotriazole monohydrate (1.47 g), and triethylamine (4.01 ml) in THF (40 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate and 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 (hexane:ethyl acetate=1:2 to ethyl acetate) to yield the entitled compound (2.12 g) as an oil.

Workup

  1. washthe organic layer was washed with water and saturated aqueous sodium chloride
  2. customdried
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to ethyl acetate)

Sources & evidence

ORD record
ord-856319c444fb45f1b3897cc92cd8b5b1
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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