Tetrahydrofuran → HCID 18333022, compound

HRID 2269736Notes

Reaction equation

HRID 2269736 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C1COCC1.[CH3:11][N:12]([CH2:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH2:16]1)[CH3:13].C(N(CC)CC)C>C(=O)(O)[O-].[K+]>[CH3:13][N:12]([CH2:14][CH:15]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:16]1)[CH3:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15542694HCID 15542694, compound

Product 1

HCID 18333022HCID 18333022, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 516893Potassium BicarbonateSolvent

Procedure

Methanesulfonyl chloride (0.6 g) was added to a THF (20 ml) solution of 3-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoline (Reference Example 44; 1 g) under ice-cooling. The reaction mixture was stirred at room temperature for 10 minutes, to which was added triethylamine (2 ml), and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was diluted with a saturated aqueous potassium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate) and recrystallized from IPE to obtain the entitled compound (1 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate)
  8. customrecrystallized from IPE

Sources & evidence

ORD record
ord-98a6af9b6ee44b4aa79429237031824a
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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