Piperazine → HCID 135895368, compound

HRID 1943702Notes

Reaction equation

HRID 1943702 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[S:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.N1CCNCC1.[Br-].[Li+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[CH:19]=[CH:20][N:21]=[CH:22][C:14]2=3)=[S:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 82050Lithium BromideHCID 86650560HCID 86650560, compound

Product 1

HCID 135895368HCID 135895368, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanethione (100 mg, 0.22 mmol) was dissolved in N,N-dimethyl formamide, and piperazine (28.4 mg, 1.5 equivalents) and lithium bromide (76.4 mg, 4 equivalents) were added thereto and then stirred at 1000 for 15 hours. N,N-dimethyl formamide was removed under reduced pressure and water was added the residue. The mixture in suspension was adjusted to pH 6 to 7 by using 1N hydrochloric acid and stirred for 30 minutes. The mixture was filtered and the resulting solid was stirred in methanol solvent and then filtered to give the target compound 51 as yellow solid (100 mg, quantitative yield).

Workup

  1. customN,N-dimethyl formamide was removed under reduced pressure and water
  2. additionwas added the residue
  3. stirringstirred for 30 minutes
  4. filtrationThe mixture was filtered
  5. stirringthe resulting solid was stirred in methanol solvent
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4ee19710b73d4a2dbc7fe4a3917be5c1
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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