Benzyl Bromide → HCID 22939103, compound

HRID 1986873Notes

Reaction equation

HRID 1986873 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[C:6]([O:25][CH3:26])=[CH:7][C:8]2[CH2:9][CH:10]3[CH2:24][NH:23][CH2:22][CH2:21][N:11]3[CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C=O.C(Cl)(Cl)Cl>[ClH:1].[ClH:1].[CH3:3][O:4][C:5]1[C:6]([O:25][CH3:26])=[CH:7][C:8]2[CH2:9][CH:10]3[CH2:24][N:23]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:22][CH2:21][N:11]3[CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]=2[CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22939098HCID 22939098, compound

Product 1

HCID 22939103HCID 22939103, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

8,9-Dimethoxy-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline dihydrochloride (the compound obtained in Example 1-(6)) (2 g) is dissolved in N,N-dimethylformamide (10 ml), and thereto are added potassium carbonate (2.8 g) and benzyl bromide (0.7 ml), and the mixture is stirred at room temperature for 3 hours. The reaction solution is diluted with chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitates (1.2 g) 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 resultant is recrystallized from ethanol to give 8,9-dimethoxy-2-benzyl-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline dihydrochloride (1.2 g).

Workup

  1. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe precipitates (1.2 g)
  5. dissolutionare dissolved in chloroform
  6. additionis added a 4M hydrochloric acid in ethyl acetate
  7. customthe solvent is removed by evaporation under reduced pressure
  8. customThe resultant is recrystallized from ethanol

Sources & evidence

ORD record
ord-7bb25e1208d74bbe9f37d42942e860e7
Source dataset
uspto-grants-2009_06
Patent number
US07550475B2

Reaction notes

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