Water → 1,3-bis[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H,3H-naphtho[1,8-cd]-1,2,6-thiadiazine 2,2-dioxide

HRID 654106Notes

Reaction equation

HRID 654106 reaction equation
[NH:1]1[S:6](=[O:8])(=[O:7])[NH:5][C:4]2[CH:9]=[CH:10][CH:11]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:2]1[C:3]=23.[H-].[Na+].Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH:26]=[C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.O>CN(C)C=O.C(OCC)(=O)C>[C:28]1([C:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][N:1]3[S:6](=[O:8])(=[O:7])[N:5]([CH2:19][CH2:20][CH2:21][N:22]4[CH2:23][CH:24]=[C:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:26][CH2:27]4)[C:4]4[CH:9]=[CH:10][CH:11]=[C:12]5[CH:13]=[CH:14][CH:15]=[C:2]3[C:3]=45)[CH2:27][CH:26]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 9025001H,3H-naphtho[1,8-cd][1,2,6]thiadiazine 2,2-dioxideHCID 98375831-(3-Chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 198884691,3-bis[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H,3H-naphtho[1,8-cd]-1,2,6-thiadiazine 2,2-dioxideYield 19.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1H,3H-naphtho[1,8-cd]-1,2,6-thiadiazine 2,2-dioxide (8.8 g) in dry N,N-dimethylformamide (20 cc) is added dropwise to a suspension of sodium hydride (1.2 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 (9.36 g) in N,N-dimethylformamide (50 cc) is added. The reaction mixture is heated to 100° C. for 1 hour and is then cooled and poured into a mixture of water (500 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 redissolved in N,N-dimethylformamide (40 cc) and the solution is diluted with ethanol (300 cc). The precipitate is filtered off, washed with ethanol and dried and then taken up in a 0.1 N aqueous sodium hydroxide solution (200 cc) in which it partially dissolves. The mixture is filtered. The insoluble material is filtered off, washed with water and dried. After recrystallization from ethyl acetate (60 cc), 1,3-bis[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H,3H-naphtho[1,8-cd]-1,2,6-thiadiazine 2,2-dioxide (2.38 g) is obtained, melting at 140° C. The filtrate obtained above is acidified to pH 4 with 1 N hydrochloric acid. The precipitate is redissolved in N,N-dimethylformamide (30 cc) at 100° C., the hot solution is filtered and is then diluted with ethanol (150 cc). The precipitate is filtered off, washed with ethanol (3×50 cc) and dried. 1-[3-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H,3H-naphtho[1,8-cd]-1,2,6-thiadiazine 2,2-dioxide (0.95 g) is obtained, melting at 240° C.

Workup

  1. temperatureis then cooled
  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. dissolutionThe residue is redissolved in N,N-dimethylformamide (40 cc)
  6. additionthe solution is diluted with ethanol (300 cc)
  7. filtrationThe precipitate is filtered off
  8. washwashed with ethanol
  9. customdried
  10. dissolutionpartially dissolves
  11. filtrationThe mixture is filtered
  12. filtrationThe insoluble material is filtered off
  13. washwashed with water
  14. customdried
  15. customAfter recrystallization from ethyl acetate (60 cc)

Sources & evidence

ORD record
ord-3dbfd7a4bec249068d48c03a72a257fd
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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