Potassium Hydroxide → HCID 59455058, compound

HRID 1400451Notes

Reaction equation

HRID 1400451 reaction equation
[Cl:1][C:2]1[C:3]([Cl:26])=[CH:4][C:5]2[CH:6]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][CH:7]3[N:8]([CH2:11][C:12](O)([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH3:13])[C:9]=2[CH:10]=1.[OH-].[K+]>S(Cl)(Cl)=O.O>[Cl:1][C:2]1[C:3]([Cl:26])=[CH:4][C:5]2[C:6]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][C:7]=3[N:8](/[CH:11]=[C:12](\[C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)/[CH3:13])[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67309406HCID 67309406, compound

Product 1

HCID 59455058HCID 59455058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

7,8-Dichloro-5-(2-hydroxy-2-(pyridin-4-yl)propyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (500 mg, 1.2 mmol) in thionylchloride (5 mL) was stirred at RT for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methyl-2-pyrrolidone (5 mL) and the solution was stirred for 5 min. at RT. Powdered KOH (482 mg, 8.5 mmol) was added and 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, concentrated under reduced pressure and the residue purified by HPLC. 1H NMR (CD3OD, formate salt) δ (ppm): 8.30 (d, 2H), 7.50 (s, 1H), 7.20 (s, 1H), 7.05 (d, 2H), 6.95 (s, 1H), 3.70 (m, 2H), 2.85 (m, 2H), 2.70 (m, 2H), 2.58 (s, 3H), 2.38 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-1211733ae18a4badb4bfee1e25d668b7
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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