Chloropyrazine → 2-[4-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)-1-piperazinyl]pyrazine

HRID 2232581Notes

Reaction equation

HRID 2232581 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[C:19]1[CH:24]=[N:23][CH:22]=[CH:21][N:20]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[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[CH2:13][CH2:14][N:15]([C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 73277ChloropyrazineHCID 81531DiisopropylethylamineHCID 4106821-(1,4-Benzodioxan-2-ylmethyl)piperazine

Product 1

HCID 143713432-[4-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)-1-piperazinyl]pyrazineYield 27.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

1-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)piperazine (2.35 g, 10 mmole), 2-chloropyrazine (1.15 g, 10 mmole) and diisopropylethylamine (1.3 g, 10 mmole) were combined in 100 ml of 1-methyl-2-pyrrolidinone and heated under N2 at 100° C. for 24 hours. Upon cooling, the solvent was removed in vacuum and the residue filtered through 75 g of silica gel using chloroform as the eluent. The product-containing fractions were combined, the solvent evaporated and the residue was crystallized from methanol with addition of 4N isopropanolic HCl. A second recrystallization from methanol gave 850 mg of title compound, as the dihydrochloride salt, m.p. 248°-253° C.(d).

Workup

  1. temperatureUpon cooling
  2. customthe solvent was removed in vacuum
  3. filtrationthe residue filtered through 75 g of silica gel
  4. customthe solvent evaporated
  5. customthe residue was crystallized from methanol with addition of 4N isopropanolic HCl
  6. customA second recrystallization from methanol

Sources & evidence

ORD record
ord-38afee5dc3a54d94983f0f65370b31c9
Source dataset
uspto-grants-1988_11
Patent number
US04788290

Reaction notes

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