Potassium Carbonate → 1-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]-4-diphenylmethylpiperazine

HRID 2268479Notes

Reaction equation

HRID 2268479 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.[C:27]1([CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.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:37]1[CH2:38][CH2:39][N:34]([CH:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:35][CH2:36]1)[CH2:18]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 183485412-(8-Iodooctyl)-4,5,6,7-tetramethoxyindan

Product 1

HCID 183486281-[8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl]-4-diphenylmethylpiperazineYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 2-(8-iodooctyl)-4,5,6,7-tetramethoxyindan (1.17 g), 1-diphenylmethylpiperazine (1.24 g) and potassium carbonate (1.70 g) in DMF (10 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 (1.19 g) 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-279b8a3511e547f4b9ee8b1afba7e57c
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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