Triethylamine → 2-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]-2H-1,4-benzothiazine-3(4H)-one

HRID 1729173Notes

Reaction equation

HRID 1729173 reaction equation
Cl[CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[S:3]1.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([N:20]2[CH2:25][CH2:24][N:23]([CH:2]3[C:7](=[O:8])[NH:6][C:5]4[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=4[S:3]3)[CH2:22][CH2:21]2)[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27600581-(4-Methylpyridin-2-yl)piperazineHCID 122185992H-1,4-Benzothiazin-3(4H)-one, 2-chloro-

Product 1

HCID 150279342-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]-2H-1,4-benzothiazine-3(4H)-oneYield 16.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

7 g (=0.035 m) of 2-chloro-2H-1,4-benzothiazine-3(4H)-one, 6.2 g of N-(4-methylpyridin-2-yl)-piperazine, and 7 g of triethylamine were heated at reflux with stirring for 5 hours in 100 ml of toluene. The suspension was worked up by diluting it with 200 ml of toluene, and the resulting precipitate was filtered out and dissolved in 20% strength aqueous hydrochloric acid solution. The solution was rendered alkaline by adding an ammonium hydroxide solution, and the resulting precipitate was filtered out, washed with water and dried. 2 g of beige-colored crystalline 2-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]-2H-1,4-benzothiazine-3(4H)-one having a melting point of 245° C. were obtained.

Workup

  1. temperatureat reflux
  2. filtrationthe resulting precipitate was filtered out
  3. dissolutiondissolved in 20% strength aqueous hydrochloric acid solution
  4. additionby adding an ammonium hydroxide solution
  5. filtrationthe resulting precipitate was filtered out
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-212a0f63b18a426292f6c77801360387
Source dataset
uspto-grants-1994_07
Patent number
US05332733

Reaction notes

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