Potassium Hydroxide → HCID 59455152, compound

HRID 1400446Notes

Reaction equation

HRID 1400446 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)(O)[CH3:14])[CH:7]3[CH2:22][CH2:23][N:24]([CH3:26])[CH2:25][CH:6]3[C:5]=2[CH:4]=1.[OH-].[K+]>S(Cl)(Cl)=O.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8](/[CH:12]=[C:13](\[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)/[CH3:14])[C:7]3[CH2:22][CH2:23][N:24]([CH3:26])[CH2:25][C:6]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67310629HCID 67310629, compound

Product 1

HCID 59455152HCID 59455152, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

1-(8-Methoxy-2-methyl-2,3,4,4a-tetrahydro-1H-pyrido[4,3-b]indol-5(9bH)-yl)-2-(pyridin-4-yl)propan-2-ol (500 mg, 1.4 mmol) was dissolved in thionylchloride (5 mL) was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methyl-2-pyrrolidone (4 mL) and stirred for 5 min. Powdered KOH (798 mg, 14.2 mmol) was added and stirring was continued at RT for additional 5 min. The reaction mixture was heated at 100° C. for 1 h. The progress of reaction was monitored by TLC and NMR. The reaction mixture was cooled at RT, diluted with water and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated and purified the compound by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.25 (d, 2H), 7.0 (m, 4H), 6.90 (d, 1H), 6.70 (d, 1H), 3.90 (m, 2H), 3.80 (s, 3H), 3.0 (t, 2H), 2.70 (s, 3H), 2.62 (m, 2H), 1.95 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in N-methyl-2-pyrrolidone (4 mL)
  3. stirringstirred for 5 min
  4. stirringstirring
  5. waitwas continued at RT for additional 5 min
  6. temperatureThe reaction mixture was heated at 100° C. for 1 h
  7. customThe progress of reaction
  8. temperatureThe reaction mixture was cooled at RT
  9. extractionextracted with EtOAc
  10. washThe organic layer was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. custompurified the compound by HPLC

Sources & evidence

ORD record
ord-629b63edd8774270bfacbcf18d397676
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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