Water → HCID 20143040, compound

HRID 649328Notes

Reaction equation

HRID 649328 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)=[CH:16][CH:15]=2)[C:5]1=[O:27].[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32]Cl.O>CN(C)C=O>[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][CH2:32][C:6]1([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)=[CH:18][CH:19]=2)[C:5](=[O:27])[N:4]([CH3:3])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 20143126HCID 20143126, compound

Product 1

HCID 20143040HCID 20143040, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of 60% sodium hydride (3.1 g) in dimethylformamide (30 ml), 3,4-dihydro-4-methyl-3-oxo-2-[4-(tetrahydropyran-2-yloxy)phenyl]-2H-1,4-benzothiazine (25.0 g) dissolved in dimethylformamide (60 ml) is added under nitrogen atmosphere, and the mixture is stirred for 30 minutes. A solution of 3-dimethylaminopropyl chloride in dimethylformamide [prepared by mixing of 3-dimethylaminopropyl chloride hydrochloride (13.3 g) and triethylamine (11.8 ml) in dimethylformamide (50 ml) and followed by filtration to remove precipitate] is added to the reaction mixture, and the mixture is stirred for 1 hour at 65°-75° C. The mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 25.1 g (81.0%) of the titled compound.

Workup

  1. additionis added under nitrogen atmosphere
  2. stirringthe mixture is stirred for 1 hour at 65°-75° C
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c772fea7ac6454195cf007ebfa9bfc6
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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