Chloroform → HCID 15592118, compound

HRID 2417601Notes

Reaction equation

HRID 2417601 reaction equation
[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]O)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)[Cl:25].S(Cl)(Cl)=O>O>[Cl:25][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:3]2[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 155921092-[4-(2-Hydroxyethyl)piperazin-1-yl]cyclohepta-2,4,6-trien-1-one

Product 1

HCID 15592118HCID 15592118, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-ethanol (10.0 g, described in Example 7), potassium carbonate (26 g) and chloroform (150 ml) was stirred and cooled in an ice-bath. Thionyl chloride (11.7 g) was added dropwise over a period of 30 min and allowed to react with stirring at room temperature for 16 hr. Water (50 ml) was added and extracted with chloroform. After drying over magnesium sulfate, the extract was evaporated and the residue (11.0 g) was chromatographed on 500 g silica gel with ethyl acetate to yield 6.2 g of 2-[4-(2-chloroethyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one mp 71°-73° C.; ir(CHCl3) 1560 cm-1 ; uv max(MeOH) 352 (ε=9730) and 255 nm(ε=14300); nmr(CDCl3) δ2.75 (m, 6H), 3.5 (m, 6H) and 7.0 (m, 5H) and Anal. Calcd for C13H17 --ClN2O: C, 61.77% H, 6.78% N, 11.08% and Found: C, 61.60% H, 6.79% N, 10.98%.

Workup

  1. temperaturecooled in an ice-bath
  2. customto react
  3. stirringwith stirring at room temperature for 16 hr
  4. extractionextracted with chloroform
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe extract was evaporated
  7. customthe residue (11.0 g) was chromatographed on 500 g silica gel with ethyl acetate

Sources & evidence

ORD record
ord-8523948aa8f1434da3b21f25676fa30b
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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