Potassium Hydroxide → 5-(2,4-dichlorophenyl)-2-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline

HRID 1789990Notes

Reaction equation

HRID 1789990 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[CH:26]3[CH2:27][N:28](C(OCC)=O)[CH2:29][CH2:30][CH:25]3[N:13]3[CH2:14][CH:15]([CH3:24])[N:16](C(OCC)=O)[C:17]([CH:18]=1)=[C:12]23.[OH-].[K+]>CCCCO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[CH:26]3[CH2:27][NH:28][CH2:29][CH2:30][CH:25]3[N:13]3[CH2:14][CH:15]([CH3:24])[NH:16][C:17]([CH:18]=1)=[C:12]23

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22036728diethyl 5-(2,4-dichlorophenyl)-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate

Product 1

HCID 220367345-(2,4-dichlorophenyl)-2-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalineYield 45%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of diethyl 5-(2,4-dichlorophenyl)-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (30 mg, 0.06 mmol) in 10 mL of n-BuOH was added KOH (33 mg, 0.6 mmol) and stirred at 120° C. for 16 h. The reaction was allowed to cool to ambient temperature and was diluted with ethyl acetate, washed with water (10 mL). The organic layer was collected and washed with 1N HCl (10 mL) and water (10 mL). This time the aqueous layer was collected and neutralized with saturated aqueous sodium bicarbonate and extracted with EtOAc (2×20 mL). The combined extracts were dried over magnesium sulfate, concentrated to afford 5-(2,4-dichlorophenyl)-2-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline (10 mg, 45%) as a solid. MS [M+H]+ 374.

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with water (10 mL)
  3. customThe organic layer was collected
  4. washwashed with 1N HCl (10 mL) and water (10 mL)
  5. customThis time the aqueous layer was collected
  6. extractionextracted with EtOAc (2×20 mL)
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-45ef0f63e0104c3c9bf0c39e4e78f987
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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