Water → HCID 15710745, compound

HRID 654109Notes

Reaction equation

HRID 654109 reaction equation
[C:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][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.O>CN(C)C=O.C(OCC)(=O)C>[C:29]1([C:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:10])=[O:9])[CH2:24][CH:25]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74296BenzenesulfonanilideHCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 15710745HCID 15710745, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A solution of N-phenylbenzenesulphonamide (2.34 g) in dry N,N-dimethylformamide (10 cc) is added dropwise to a suspension of sodium hydride (0.24 g, 80% suspension in oil) in N,N-dimethylformamide (50 cc). After 15 minutes' stirring, a solution of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine (2.34 g) in N,N-dimethylformamide (20 cc) is added. The reaction mixture is heated to 140° C. for 1 hour and then cooled and poured into a mixture of water (200 cc) and ethyl acetate (200 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, 40-cm height) and eluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc being collected. Fractions 5 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After recrystallization from isopropyl ether (150 cc), N-[3-(4-phenyl-1,2,3,6-tetrahydropyridyl)propyl]-N-phenylbenzenesulphonamide (2.4 g) is obtained, melting at 112° C.

Workup

  1. temperaturecooled
  2. washThe organic phase is washed with water
  3. dry with materialis dried over magnesium sulphate
  4. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a column of silica gel (0.2-0.063-mm particle size, 4-cm diameter, 40-cm height)
  6. washeluted with dichloromethane and with a mixture of dichloromethane and ethanol (98-2 and 96-4 by volume), fractions 250-cc
  7. custombeing collected
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customAfter recrystallization from isopropyl ether (150 cc)

Sources & evidence

ORD record
ord-e41f848d6e1343cd98e5354142b9a2f4
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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