Sulfuric Acid → HCID 59368403, compound

HRID 1045578Notes

Reaction equation

HRID 1045578 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:26])[CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:11]2=3)=[CH:4][CH:3]=1.OS(O)(=O)=O.[OH-].[K+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[CH3:26])=[CH:9]/[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:11]2=3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 59368274HCID 59368274, compound

Product 1

HCID 59368403HCID 59368403, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The title compound was prepared by following general procedure 6. 2-(4-Chlorophenyl)-1-(3,9-dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)propan-2-ol (100 mg, 0.261 mmol) was taken into 2.0 mL of 25% H2SO4 in water, and stirred at 90° C. for 2 h. The reaction was monitored by LCMS. The reaction mixture was cooled and basified with aq. KOH solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified using reverse phase chromatography to afford 10 mg of product as the TFA salt along with 6-(2-(4-chlorophenyl)allyl)-3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-743a8fb0caaa430881eb1ed08f02207a
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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