N-methyl-2-pyrrolidone → HCID 68487059, compound

HRID 1401466Notes

Reaction equation

HRID 1401466 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+].[C:18]1([C:24]2[CH:29]=[CH:28]N=C[CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1.[CH3:30][N:31]1CCCC1=O>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH:23]3[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]3[C:24]3[CH:25]=[N:31][CH:30]=[CH:28][CH:29]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 13319495HCID 13319495, compound

Product 1

HCID 68487059HCID 68487059, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.1 g, 0.45 mmol) in N-methyl-2-pyrrolidone (1.0 mL) was added powdered KOH (0.140 g, 2.5 mmol) and stirred for 10 min. at RT. 4-cyclohexenylpyridine (1.25 mol) was added and the reaction mixture was stirred for additional 4 h at 100° C. After completion of reaction (as analyzed by TLC), the reaction mixture was diluted with water (15 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the product.

Workup

  1. stirringthe reaction mixture was stirred for additional 4 h at 100° C
  2. customAfter completion of reaction (as analyzed by TLC)
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the product

Sources & evidence

ORD record
ord-3d20be74d9d94113b1f74a85b25ef7f5
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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