Ethyl Acetate → HCID 18377271, compound

HRID 2301124Notes

Reaction equation

HRID 2301124 reaction equation
C(O[C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[CH3:22])=O)(C)(C)C.BrC[CH2:25][CH2:26][CH2:27][C:28]12[CH2:39][CH2:38][CH2:37][C:35]3[C:36]1=[C:31]([CH:32]=[CH:33][CH:34]=3)[NH:30][C:29]2=[O:40].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.Cl>[CH3:19][O:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:20][CH3:21])[CH:9]([CH3:22])[N:8]([CH2:6][CH2:25][CH2:26][CH2:27][C:28]13[CH2:39][CH2:38][CH2:37][C:35]4[C:36]1=[C:31]([CH:32]=[CH:33][CH:34]=4)[NH:30][C:29]3=[O:40])[CH2:17][CH2:16]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneHCID 15173293HCID 15173293, compound

Product 1

HCID 18377271HCID 18377271, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

2-t-Butoxycarbonyl-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline (190 mg, 0.61 mmol) was dissolved in hydrochloric acid methanol solution (4 ml) and stirred at room temperature for 2.5 hours. The residue obtained by evaporating the solvent from the reaction solution under a reduced pressure was dissolved in anhydrous N,N-dimethylformamide (2 ml), and the solution was mixed with 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indole-2-one (190 mg, 0.61 mmol) and potassium carbonate (250 mg, 1.8 mmol) and stirred at room temperature for 14 hours. The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 200 mg (0.46 mmol, 76% in yield) of the title compound.

Workup

  1. customThe residue obtained
  2. customby evaporating the solvent from the reaction solution under a reduced pressure
  3. dissolutionwas dissolved in anhydrous N,N-dimethylformamide (2 ml)
  4. stirringstirred at room temperature for 14 hours
  5. washwashed with water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation under a reduced pressure
  8. customthe thus obtained material was separated
  9. custompurified by a silica gel column chromatography
  10. customto obtain

Sources & evidence

ORD record
ord-2b56d00aa7024ccfa8784d2473d1bc09
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

Loading…