Potassium Carbonate → HCID 9911534, compound

HRID 365310Notes

Reaction equation

HRID 365310 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=2)[CH2:25][CH2:24]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[N:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][C:30]=1[CH2:29][N:26]1[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][O:1][C:2]2[CH:12]=[CH:11][C:5]3[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=3[CH:3]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8200317-hydroxy-2H-1,4-benzothiazin-3(4H)-oneHCID 23291076HCID 23291076, compound

Product 1

HCID 9911534HCID 9911534, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

After a mixture consisting of 7-hydroxy-3,4-dihydro-2H-1,4-benzothiazin-3-one (1.812 g, 10 mmol), tetra-n-butylammonium bromide (0.322 g, 1 mmol), potassium carbonate (2.764 g, 20 mmol), 1-(3-chloropropyl)-4-(2-quinolylmethyl)piperazine (3.039 g, 10 mmol) and N,N-dimethylformamide (40 ml) was stirred for 4 days at a bath temperature of 50° C. under an argon gas stream, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with chloroform. The extract was washed with water and then dried over anhydrous magnesium sulfate. The extract was subjected to chromatography on a silica gel column (developer: chloroform/methanol=100/1 to 40/1) and then crystallized from ethyl acetate, whereby 1.188 g of the title compound were obtained as yellow prisms (yield: 26.5%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-af01e7c9f51a47cda281f4f4687ff61b
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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