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

HRID 1107419Notes

Reaction equation

HRID 1107419 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 litres 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-e7482fb1bb304448be23953d72a03168
Source dataset
uspto-grants-2000_05
Patent number
US06060487

Reaction notes

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