Triethylamine → HCID 22939109, compound

HRID 1986883Notes

Reaction equation

HRID 1986883 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.[Cl:25][CH2:26][S:27][CH3:28].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[ClH:25].[ClH:25].[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]([CH2:26][S:27][CH3:28])[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

6

Reactant 3

HCID 8471TriethylamineHCID 16916Chloromethyl methyl sulfideHCID 9883736HCID 9883736, compound

Product 1

HCID 22939109HCID 22939109, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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)) (3.2 g) is dissolved in methylene chloride (20 ml), and thereto are added chloromethyl methylsulfide (8.4 ml), triethylamine (3.5 ml) and 4-(dimethylamino)pyridine (61 mg), and the mixture is stirred at room temperature overnight. The reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=9:1). The resulting precipitates (115 mg) are 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 residue is recrystallized from ethanol to give 8,9-dimethoxy-2-(methylthiomethyl)-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline dihydrochloride (60 mg).

Workup

  1. washThe reaction solution is washed with a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=9:1)
  5. customThe resulting precipitates (115 mg)
  6. dissolutionare 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 residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-f6ba24002a3d42259fe3733f0f3d1b79
Source dataset
uspto-grants-2009_06
Patent number
US07550476B2

Reaction notes

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