Methanol → HCID 23077618, compound

HRID 1349494Notes

Reaction equation

HRID 1349494 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Br-:32].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[C:11]([Br:32])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24437Sodium SulfiteHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 23077716HCID 23077716, compound

Product 1

HCID 23077618HCID 23077618, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 9-benzyloxy-2-(3,4-dichlorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (3.8 g) obtained in Example 1, Step 3 in chloroform (90 ml)-methanol (60 ml) was added phenyltrimethylammonium tribromide (5.0 g) and the mixture was stirred at room temperature for 13 hr. An aqueous sodium sulfite solution was added to the reaction mixture and the mixture was extracted twice with chloroform. The combined extract was washed with brine and purified as it was by silica gel column chromatography (chloroform-methanol=19:1–10:1) to give 9-benzyloxy-7-bromo-2-(3,4-dichlorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (2.44 g).

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. extractionThe combined extract
  3. washwas washed with brine
  4. custompurified as it

Sources & evidence

ORD record
ord-f715d5119cb3452ab0bb023262c7ab2e
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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