Morpholine → HCID 59054066, compound

HRID 2407990Notes

Reaction equation

HRID 2407990 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)[CH2:12][C:11]2([CH3:26])[CH3:25])(=[O:7])=[O:6])([CH3:3])[CH3:2].Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>CS(C)=O.[Cu]I>[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:19]=1)[CH2:12][C:11]2([CH3:26])[CH3:25])(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 70497035HCID 70497035, compound

Product 1

HCID 59054066HCID 59054066, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

The mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid isopropylamide (392.0 mg, 0.9 mmol), CuI (51.0 mg, 0.27 mmol), N,N-dimethylglycine hydrochloride (75.0 mg, 0.54 mmol), potassium carbonate (373.0 mg, 2.7 mmol) and morpholine (0.78 mL, 9.0 mmol) in DMSO (5.0 mL) was stirred at 120° C. for 16 h under a nitrogen atmosphere. Then the reaction mixture was cooled to room temperature and extracted with ethyl acetate (70 mL×2), washed with water (30 mL×3) and saturated aqueous ammonium chloride solution (30 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid isopropylamide (160.0 mg, 40%) as a light yellow solid: MS (ESI) M+1=444.3.

Workup

  1. extractionextracted with ethyl acetate (70 mL×2)
  2. washwashed with water (30 mL×3) and saturated aqueous ammonium chloride solution (30 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-c084f5b340494ebcbe70e6438c8493c8
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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