1,2,3,4-Tetrahydroisoquinoline → HCID 12049559, compound

HRID 2187042Notes

Reaction equation

HRID 2187042 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:2][CH2:3][CH2:4][CH2:5][C@@:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18]

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15887274HCID 15887274, compound

Product 1

HCID 12049559HCID 12049559, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (120 mg, 0.40 mmol), 1,2,3,4-tetrahydroisoquinoline (59 mg, 0.44 mmol), and potassium carbonate (83 mg, 0.60 mmol) in anhydrous N,N-dimethylformamide (1 ml) were stirred at room temperature for 2 days. To the reaction mixture obtained was added ethyl acetate (80 ml), which was then washed with water and saturated saline solution. After drying with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a product. The product obtained was separated and purified by means of silica gel column chromatography, whereby 150 mg (0.40 mmol, yield 100%) of the above-described object compound could be obtained.

Workup

  1. customTo the reaction mixture obtained
  2. washwas then washed with water and saturated saline solution
  3. dry with materialAfter drying with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customto obtain a product
  6. customThe product obtained
  7. customwas separated

Sources & evidence

ORD record
ord-f710028f426e439c83edcb9713357fcd
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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