Potassium Hydroxide → HCID 66764905, compound

HRID 574614Notes

Reaction equation

HRID 574614 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[NH:6]2.[OH-].[K+].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CS(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[N:6]2[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 404239934,6-Dichloro-2-methyl-1H-indole

Product 1

HCID 66764905HCID 66764905, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4,6-dichloro-2-methylindole (75 mg, 0.37 mmol) in 0.5 mL DMSO was added pulverized KOH (95 mg, 1.69 mmol), then 2-chloroethylmorpholine HCl (140 mg, 0.75 mmol) and the reaction stirred at room temperature overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 10% MeOH in CH2Cl2 to give a final yield of 91 mg (0.29 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.42-2.55 (m, 4H), 2.44 (s, 3H), 2.60 (t, J=7.0 Hz, 2H), 3.65-3.79 (m, 4H), 4.08 (t, J=7.0 Hz, 2H), 6.31 (s, 1H), 7.09 (s, 1H), 7.16 (s, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.84, 41.59, 54.10, 57.79, 66.91, 98.99, 107.84, 119.47, 125.23, 125.51, 126.17, 137.22, 138.20. MS m/z 313.5 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between H2O and toluene
  2. extractionthe organic extract
  3. washwashed two times with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified via silica gel chromatography
  8. customto give a final yield of 91 mg (0.29 mmol)

Sources & evidence

ORD record
ord-323a5c051d66438e94d417f9b05ba9f4
Source dataset
uspto-grants-2015_05
Patent number
US09034895B2

Reaction notes

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