2,6-Dichloropyrazine → 2-Chloro-6-[4-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-piperazinyl]pyrazine

HRID 2232579Notes

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[CH:24]=[N:23][CH:22]=[C:21](Cl)[N:20]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([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:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)piperazine (4.7 g, 20 mmole) and 2,6-dichloropyrazine (3.0 g, 20 mmole) were combined in 200 ml of dimethylformamide and 2.6 g (20 mmole) of diisopropylethylamine was added. The mixture was heated under nitrogen at 60° C. for 24 hours. The solvent was then removed in vacuum and the residue filtered through 75 g of silica gel with chloroform as the eluent. The product-containing fractions were concentrated in vacuum and the residue was crystallized from methanol with addition of 4N isopropanolic HCl and recrystallized from methanol to give 4.26 g of the title compound as the monohydrochloride, m.p. 270°-280° C.

Workup

customThe solvent was then removed in vacuum
filtrationthe residue filtered through 75 g of silica gel with chloroform as the eluent
concentrationThe product-containing fractions were concentrated in vacuum
customthe residue was crystallized from methanol with addition of 4N isopropanolic HCl
customrecrystallized from methanol

Sources & evidence

ORD record: ord-9471c9d934044d948908ce99230571ed
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788290

Reaction notes

Loading…