2,3-Dichloropyrazine → 2-Chloro-3-[4-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-piperazinyl]pyrazine

HRID 2232580Notes

Reaction equation

HRID 2232580 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[Cl:18][C:19]1[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:18][C:19]1[C:24]([N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH:2]3[O:1][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3]3)[CH2:17][CH2:16]2)=[N:23][CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 785752,3-DichloropyrazineHCID 81531DiisopropylethylamineHCID 4106821-(1,4-Benzodioxan-2-ylmethyl)piperazine

Product 1

HCID 143713422-Chloro-3-[4-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-piperazinyl]pyrazineYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

1-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)piperazine (2.35 g, 10 mmole), 2,3-dichloropyrazine (1.5 g, 10 mmole) and diisopropylethylamine (1.3 g, 10 mmole) were combined in 100 ml of dimethylformamide and heated at 75° C. under N2 for 24 hours. The solvent was removed in vacuum and the residue was filtered through 75 g of silica gel using choroform as the eluent. The relevant fractions were combined, the solvent evaporated and the residue crystallized from isopropanol with addition of 4N isopropanolic HCl to give 2.1 g of title compound as the hydrochloride, m.p. 217°-218° C.

Workup

  1. customThe solvent was removed in vacuum
  2. filtrationthe residue was filtered through 75 g of silica gel
  3. customthe solvent evaporated
  4. customthe residue crystallized from isopropanol with addition of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-0ef34afae9364804a4923bac8e3d1db4
Source dataset
uspto-grants-1988_11
Patent number
US04788290

Reaction notes

Loading…