Sodium Chloride → 1-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine

HRID 1087555Notes

Reaction equation

HRID 1087555 reaction equation
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([C:18]([OH:20])=O)=[C:8]2[N:3]1[CH:4]=[CH:5][C:6]1[CH:23]=[CH:22][S:21][C:7]=12.S(Cl)(Cl)=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[Cl-].[Na+]>O1CCOCC1.O>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:18]([C:9]2[CH:10]=[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:2](=[O:1])[N:3]3[C:8]=2[C:7]2[S:21][CH:22]=[CH:23][C:6]=2[CH:5]=[CH:4]3)=[O:20])[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 146667437-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid

Product 1

HCID 147700761-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.93 g of 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylic acid were converted into the acid chloride with 2.65 ml of thionyl chloride as described. This acid chloride was taken up in 80 ml of dioxane, treated with 2.7 ml of N-methylpiperazine, and the mixture was then stirred at room temperature until the reaction was completed and poured into 200 ml of water. The aqueous phase was saturated with sodium chloride and extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. By recrystallization from toluene there was obtained 1-methyl-4-[(7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizin-10-yl)carbonyl]piperazine as yellow crystals of m.p. 233°-234° (dec.).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customBy recrystallization from toluene

Sources & evidence

ORD record
ord-6e308a4698204932accf79c9f7fa3056
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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