Dimethylformamide → 2-[4-(2,3-Dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-one

HRID 619106Notes

Reaction equation

HRID 619106 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:11][CH3:12])=[CH:7][CH:8]=2)[C:3]1=[O:13].[O:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:18]=2[O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:14]1[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([N:24]3[CH2:29][CH2:28][N:27]([CH:2]4[CH2:10][C:9]5[C:4](=[CH:5][C:6]([O:11][CH3:12])=[CH:7][CH:8]=5)[C:3]4=[O:13])[CH2:26][CH2:25]3)[C:18]=2[O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 65853EltoprazineHCID 110967482-Bromo-6-methoxy-1-indanone

Product 1

HCID 109925342-[4-(2,3-Dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxyindan-1-oneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension prepared from 25.3 g (100 mmol) of the compound obtained in Step 1, 22.0 g (100 mmol) of (2,3-dihydro[1,4]benzodioxin-5-yl)piperazine, 13.8 g (100 mmol) of potassium carbonate and 140 ml of dimethylformamide is stirred at room temperature for 20 hours. The mixture is then poured into 1.5 liters of water, and the solid that forms (violet) is filtered off, rinsed with water and dried in vacuo to obtain 28.1 g of the expected product.

Workup

  1. filtrationthe solid that forms (violet) is filtered off
  2. washrinsed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5d3217cb2c884d308a3102d0a4776d97
Source dataset
uspto-grants-1999_09
Patent number
US05958927

Reaction notes

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