Potassium Hydroxide → HCID 59455106, compound

HRID 1401528Notes

Reaction equation

HRID 1401528 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 59455106HCID 59455106, 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) in thionylchloride (5 mL) and stirred at RT for 2 h. The reaction mixture was concentrated followed under reduced pressure. The residue was dissolved in N-methyl-2-pyrrolidone (4 mL) and the solution was stirred for 5 min. at RT. Powdered KOH (798 mg, 14.2 mmol) was added, the reaction mixture was stirred at RT for 5 min. and then at 100° C. for 1 h. The progress of reaction was monitored by TLC and NMR. Upon completion 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, concentrated under reduced pressure and the residue purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.58 (d, 2H), 7.70 (d, 2H), 7.30 (s, 1H), 7.10 (d, 1H), 6.95 (s, 1H), 6.80 (d, 1H), 3.95 (s, 2H), 3.80 (s, 3H), 3.10 (t, 2H), 2.90 (t, 2H), 2.70 (s, 3H), 2.0 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in N-methyl-2-pyrrolidone (4 mL)
  3. stirringthe reaction mixture was stirred at RT for 5 min.
  4. waitat 100° C. for 1 h
  5. customThe progress of reaction
  6. temperatureUpon completion the reaction mixture was cooled at RT
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-232a0dc9d21945b2b41a0ac9dd3a3e46
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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