Benzoyl chloride → HCID 22939115, compound

HRID 859940Notes

Reaction equation

HRID 859940 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:23][CH3:24])=[CH:5][C:6]2[CH2:7][CH:8]3[CH2:22][NH:21][CH2:20][CH2:19][N:9]3[CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]=2[CH:12]=1.C(N(CC)CC)C.[C:32]([Cl:40])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[ClH:40].[CH3:1][O:2][C:3]1[C:4]([O:23][CH3:24])=[CH:5][C:6]2[CH2:7][CH:8]3[CH2:22][N:21]([C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:20][CH2:19][N:9]3[CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 9883736HCID 9883736, compound

Product 1

HCID 22939115HCID 22939115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8,9-Dimethoxy-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline (the compound obtained in Example 1-(6)) (1.6 g) is dissolved in methylene chloride (10 ml), and thereto are added triethylamine (0.8 ml) and benzoyl chloride (0.6 ml) under ice-cooling, and the mixture is stirred for 30 minutes. The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=9:1). The resulting residue is dissolved in chloroform, and thereto is added a 4M hydrochloric acid in ethyl acetate, and the solvent is removed by evaporation under reduced pressure. The resultant is crystallized from ethyl acetate, and the crystals thus obtained are collected by filtration to give 8,9-dimethoxy-2-benzoyl-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline hydrochloride (656 mg).

Workup

  1. temperaturecooling
  2. washThe reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=9:1)
  6. dissolutionThe resulting residue is dissolved in chloroform
  7. additionis added a 4M hydrochloric acid in ethyl acetate
  8. customthe solvent is removed by evaporation under reduced pressure
  9. customThe resultant is crystallized from ethyl acetate
  10. customthe crystals thus obtained
  11. filtrationare collected by filtration

Sources & evidence

ORD record
ord-b1d53dbb987147c8ac40027cb6f9ba59
Source dataset
uspto-grants-2006_12
Patent number
US07153859B2

Reaction notes

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