Hydrochloric Acid → HCID 19101549, compound

HRID 1974473Notes

Reaction equation

HRID 1974473 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7]1.Cl.[C:19]1([C:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1>[CH3:13][N:10]1[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:28]2[CH2:27][CH:26]=[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:30][CH2:29]2)[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochlorideHCID 15027933HCID 15027933, compound

Product 1

HCID 19101549HCID 19101549, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.4 g (=0.0076 m) of 2-(4-bromobutyl)-4-methyl-2H-1,4-benzothiazine-3(4H)-one, 1.49 g (=0.0076 m) of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride and 3.09 g of triethylamine were introduced into 20 ml of toluene. The resulting suspension was heated for 10.5 hours with stirring. The mixture was worked up by cooling and introducing the suspension into 30 ml of 20% strength aqueous hydrochloric acid solution. The resulting precipitate was filtered out, and the aqueous phase was rendered alkaline and extracted with 200 ml of dichloromethane. The precipitate was introduced into an aqueous alkaline solution and extracted with 450 ml of dichloromethane. The combined dichloromethane extracts were washed, dried over sodium sulfate, and the solvent was distilled off. 2.1 g of 4-methyl-2-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)-butyl]-2H-1,4-benzothiazine-3(4H)-one were obtained as a beige-colored powder.

Workup

  1. temperatureThe resulting suspension was heated for 10.5 hours
  2. temperatureby cooling
  3. filtrationThe resulting precipitate was filtered out
  4. extractionextracted with 200 ml of dichloromethane
  5. additionThe precipitate was introduced into an aqueous alkaline solution
  6. extractionextracted with 450 ml of dichloromethane
  7. washThe combined dichloromethane extracts were washed
  8. dry with materialdried over sodium sulfate
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-de862a2066424a158721c3ba3cba0274
Source dataset
uspto-grants-1994_02
Patent number
US05283243

Reaction notes

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