Potassium Hydroxide → HCID 68488087, compound

HRID 1400424Notes

Reaction equation

HRID 1400424 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[N:12]1[C:20]2[CH:19]=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[C:14]2[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:13]1=2)(=O)=O.[OH-].[K+]>CN1C(=O)CCC1.O>[C:7]1([N:12]2[C:20]3[CH:19]=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[C:14]3[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:13]2=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86644756HCID 86644756, compound

Product 1

HCID 68488087HCID 68488087, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)yl)cyclohexyl methanesulfonate (0.33 g, 0.87 mmol) in NMP (3 mL), KOH (0.49 g, 8.7 mmol) was added at RT. The reaction mixture was heated overnight at 120° C. The reaction was monitored by LCMS. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure and purified by column chromatography (silica gel 3% MeOH in DCM) to afford 200 mg of the desired product. 1H NMR (CDCl3, HCl salt) δ (ppm): 7.50 (d, 2H), 7.40 (d, 2H), 7.23 (d, 1H), 7.1-7.0 (m, 2H), 6.9 (s, 1H), 3.8 (s, 2H), 3.0-2.8 (m, 4H), 2.6 (s, 3H), 2.45 (s, 3H), 2.0 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel 3% MeOH in DCM)

Sources & evidence

ORD record
ord-ac5ae2707adf46a7af0e25eb4ffa43c4
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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