Water → HCID 54211665, compound

HRID 654100Notes

Reaction equation

HRID 654100 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:9][CH2:8][CH2:7][N:6]3[S:5]1(=[O:17])=[O:16].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][N:4]3[C:14]4=[C:15]5[C:10](=[CH:11][CH:12]=[CH:13]4)[CH2:9][CH2:8][CH2:7][N:6]5[S:5]3(=[O:17])=[O:16])[CH2:27][CH2:26]2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 10923705HCID 10923705, compound

Product 1

HCID 54211665HCID 54211665, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2-chloroethyl)-5,6-dihydro-(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (3.4 g), 4-(4-fluorophenyl)piperazine (2.25 g) and triethylamine (1.75 cc) in dry N,N-dimethylformamide (50 cc) is heated to reflux for 3 hours and is then cooled and poured into a mixture of water (300 cc) and ethyl acetate (300 cc). The organic phase is washed with water (3×200 cc), is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 50-cm height) and eluted at a pressure of 0.7 bars of nitrogen with a mixture of cyclohexane and ethyl acetate (80-20 by volume), 125-cc fractions being collected. Fractions 33 to 43 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from isopropyl ether (50 cc), 1 -[2-(4-(4-fluorophenyl)-1-piperazinyl)ethyl]-5,6-dihydro(1H,4H)-1,2,5-thiadiazolo[4,3,2-ij]quinoline 2,2-dioxide (0.85 g) is obtained, melting at 118° C.

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureis then cooled
  3. washThe organic phase is washed with water (3×200 cc)
  4. dry with materialis dried over magnesium sulphate
  5. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 50-cm height)
  7. washeluted at a pressure of 0.7 bars of nitrogen with a mixture of cyclohexane and ethyl acetate (80-20 by volume), 125-cc fractions
  8. custombeing collected
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  10. customAfter recrystallization from isopropyl ether (50 cc)

Sources & evidence

ORD record
ord-cefc974000d24d9689a8ac3516c9b8d3
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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