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Dimethylamine, hydrochloride → N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]-N,N-dimethylamine

HRID 2268474
Notes
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Reaction equation

HRID 2268474 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[C:13]([O:25][CH3:26])[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]=2[O:19][CH3:20])[CH2:11]1.Cl.[CH3:28][NH:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:26][O:25][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[C:16]([O:19][CH3:20])=[C:17]2[C:12]=1[CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:29]([CH3:30])[CH3:28])[CH2:18]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 183485412-(8-Iodooctyl)-4,5,6,7-tetramethoxyindan

Product 1

HCID 18348536N-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]-N,N-dimethylamineYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

The mixture of 2-(8-iodooctyl)-4,5,6,7-tetramethoxyindan (1.20 g), dimethylamine hydrochloride (411 mg) and potassium carbonate (1.74 g) in DMF (12 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and 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 alumina column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (620 mg) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (hexane to hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f3f77029c0d34110af48b9634745dd60
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes