Water → 6-[3-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide hydrogen oxalate

HRID 654103Notes

Reaction equation

HRID 654103 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.[OH2:35].[C:36]([O:39]CC)(=[O:38])[CH3:37]>CN(C)C=O>[C:36]([OH:39])(=[O:38])[C:37]([OH:11])=[O:35].[C:29]1([C:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][N:9]3[C:8]4[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=4[C:6]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:10]3(=[O:12])=[O:11])[CH2:24][CH:25]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 7080916~{h}-Benzo[c][1,2]benzothiazine 5,5-DioxideHCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 198884666-[3-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide hydrogen oxalate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
100 °C

Procedure

A solution of 6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide (5.6 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.72 g, 80% suspension in oil) in N,N-dimethylformamide (40 cc). After 30 minutes' stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (5.6 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 100° C. for 30 minutes and to reflux for 30 minutes 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, 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 with dichloromethane and then a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), 250-cc fractions being collected. Fractions 8 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in boiling ethanol (200 cc). The hot solution is filtered and treated with a solution of oxalic acid (2 g) in ethanol (20 cc). After cooling, the crystals are filtered off, washed with ethanol and dried. 6-[3-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide hydrogen oxalate (7 g) is obtained, melting at 170° C. (dec.).

Workup

  1. temperatureto reflux for 30 minutes
  2. temperatureis then cooled
  3. washThe organic phase is washed with water
  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 with dichloromethane
  8. additiona mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), 250-cc fractions
  9. custombeing collected
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  11. dissolutionThe residue is dissolved
  12. filtrationThe hot solution is filtered
  13. additiontreated with a solution of oxalic acid (2 g) in ethanol (20 cc)
  14. temperatureAfter cooling
  15. filtrationthe crystals are filtered off
  16. washwashed with ethanol
  17. customdried

Sources & evidence

ORD record
ord-b4728ed947224a18920299ad93ebb636
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

Loading…