Diethyl Oxalate → HCID 13457890, compound

HRID 462724Notes

Reaction equation

HRID 462724 reaction equation
Cl.Cl.[CH3:3][NH:4][CH2:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][NH:7]1.C(N(CC)CC)C.C([O:31][C:32](=O)[C:33](OCC)=[O:34])C>C(Cl)(Cl)Cl>[CH3:3][N:4]1[C:32](=[O:31])[C:33](=[O:34])[N:7]2[CH2:8][C@@H:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[C:15]([C@@H:6]2[CH2:5]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 8471TriethylamineHCID 70409025HCID 70409025, compound

Product 1

HCID 13457890HCID 13457890, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of cis-1,2,3,4-tetrahydro-1-methylaminomethyl-4-phenylisoquinoline dihydrochloride (30.6 g, 0.094 m) in chloroform (500 ml) maintained under nitrogen at ambient temperature was added triethylamine (42.6 g, 0.42 m) and then in one portion diethyloxalate (30.1 g, 0.206 m) and the mixture heated to reflux for 4 hours. The mixture was cooled and washed with 10% HCl (3×150 ml) and water (150 ml), then dried over MgSO4. The solvent was evaporated to give 22.3 g of cis-1,3,4,6,7,11b-hexahydro-2-methyl-7-phenyl-2H-pyrazino[2,1-a]isoquinoline-3,4-dione as a pale yellow solid. An analytical sample, recrystallized from isopropanol, had m.p. 193°-194°.

Workup

  1. temperatureto reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. washwashed with 10% HCl (3×150 ml) and water (150 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6d9a3d78e4a6467aa909b9d54b187a1a
Source dataset
uspto-grants-1985_05
Patent number
US04517187

Reaction notes

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