Sodium hydride → 5-[(2,6-dimethoxyphenyl)methyl]-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

HRID 543546

Reaction equation

HRID 543546 reaction equation
[N:1]1[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][CH:8]3[C:7](=[O:14])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:22]=1[CH2:23]Cl>CN(C)C=O>[CH3:30][O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH3:19])[C:22]=1[CH2:23][N:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:10]=2[N:9]2[CH2:11][CH2:12][CH2:13][CH:8]2[C:7]1=[O:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27661876a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-oneHCID 127070022-(chloromethyl)-1,3-dimethoxyBenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 133420805-[(2,6-dimethoxyphenyl)methyl]-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (2.7 g. 0.01 mole) in 30 ml. of dry dimethyl formamide was added sodium hydride (0.5 g., 0.02 mole of 50% dispersion in mineral oil). When the evolution of hydrogen subsides, 2.7 g. (0.01 mole) of 2,6-dimethoxybenzyl chloride was added. The reaction mixture was stirred at room temperature for eighteen hours, and the dimethyl formamide was removed under vacuo. The residue was triturated with cold water, filtered and recrystallized from ethanol to give white crystals of the title compound, 2.7 g. (89% yield) m.p. 200°-202° C.; hydrochloride salt, m.p. 220°-223° C.

Workup

  1. customthe dimethyl formamide was removed under vacuo
  2. customThe residue was triturated with cold water
  3. filtrationfiltered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6583a93d32e343f8b31f9da4155b9909
Source dataset
uspto-grants-1984_05
Patent number
US04446323

Linked notes

Loading…