Water → HCID 19759191, compound

HRID 1086858Notes

Reaction equation

HRID 1086858 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][CH:13]=[C:12]([C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])[C:11]=2[CH:23]=1)(=[O:5])=[O:4].[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)=[CH2:25].[OH2:32].[OH2:33].O.[C:35]([O-:38])(=[O:37])[CH3:36].[Na+].O>CO>[C:36]([OH:33])(=[O:32])[C:35]([OH:38])=[O:37].[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][CH:13]=[C:12]([C:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:25][CH2:24][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:19][CH2:18]3)=[O:16])[C:11]=2[CH:23]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 75212-VinylpyridineHCID 19759190HCID 19759190, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 19759191HCID 19759191, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.80 g (0.00213 mole) of the piperidine derivative, 0.45 g (0.00427 mol) of 2-vinylpyridine, 0.435 g (0.0032 mol) of sodium acetate trihydrate, 2 mL of water and 2 mL of methanol was stirred and refluxed for 15 hours. The solution was evaporated to dryness and the residue was purified by flash chromatography on silica gel using 5% CH3OH in chloroform saturated with ammonia as an eluant. The chromatographically homogeneous fractions were combined. An oxalate salt, prepared in isopropyl alcohol-ethanol, was recrystallized from water to five the title compound, mp. 206°-208° C. Anal. Calc'd. for C22H25N3O3S2.2C2H2O4 : C, 50.07; H, 4.69; N, 6.74. Found: C, 50.05; H, 4.61; N, 6.76.

Workup

  1. temperaturerefluxed for 15 hours
  2. customThe solution was evaporated to dryness
  3. customthe residue was purified by flash chromatography on silica gel using 5% CH3OH in chloroform saturated with ammonia as an eluant
  4. customAn oxalate salt, prepared in isopropyl alcohol-ethanol
  5. customwas recrystallized from water to five the title compound, mp. 206°-208° C

Sources & evidence

ORD record
ord-bf71a02d07f343b29a7d10c4216183f4
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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