Butylamine → HCID 19063101, compound

HRID 482487Notes

Reaction equation

HRID 482487 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:30])[CH2:24][C:25](OCC)=[O:26])[CH2:19][CH2:18]2)[N:4]=1.[CH2:31]([NH2:35])[CH2:32][CH2:33][CH3:34]>CS(C)=O>[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:30])[CH2:24][C:25]([NH:35][CH2:31][CH2:32][CH2:33][CH3:34])=[O:26])[CH2:19][CH2:18]2)[N:4]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 19063096HCID 19063096, compound

Product 1

HCID 19063101HCID 19063101, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4 g of the compound prepared in Example 18 and 30 ml of n-butylamine in 10 ml DMSO is warmed at 140° C. for 20 h in a closed flask. The solution is evaporated under vacuum, the oily residue is treated with 200 ml H2O and extracted with CHCl3 (3×50 ml). The vitrous residue, obtained by evaporating the organic phase, is dissolved in 40 ml EtOH 95%, the solution is added with 10 ml KOH 0.3N and warmed to reflux for 30'. The residue obtained by evaporation of the solution is purified by flash chromatography on SiO2 column eluting with a CHCl3 /MeOH gradient from 100:3 to 100:10. The crude product, obtained by evaporating the fractions containing the pure compound, is dissolved in 75 ml EtOH, the solution acidified with HCl in EtOH 4N and the hydrochloride is collected by filtration, crystallized from EtOH 90% giving 2.5 g (53%) of the wanted compound; m.p.: 260°-262° C.

Workup

  1. customThe solution is evaporated under vacuum
  2. additionthe oily residue is treated with 200 ml H2O
  3. extractionextracted with CHCl3 (3×50 ml)
  4. customThe vitrous residue, obtained
  5. customby evaporating the organic phase
  6. dissolutionis dissolved in 40 ml EtOH 95%
  7. additionthe solution is added with 10 ml KOH 0.3N
  8. temperaturewarmed
  9. temperatureto reflux for 30'
  10. customThe residue obtained by evaporation of the solution
  11. customis purified by flash chromatography on SiO2 column
  12. washeluting with a CHCl3 /MeOH gradient from 100:3 to 100:10
  13. customThe crude product, obtained
  14. customby evaporating the fractions
  15. additioncontaining the pure compound
  16. dissolutionis dissolved in 75 ml EtOH
  17. filtrationthe hydrochloride is collected by filtration
  18. customcrystallized from EtOH 90%

Sources & evidence

ORD record
ord-ce7523307c5e4bf7bb092a01d85f4cc6
Source dataset
uspto-grants-1998_08
Patent number
US05798362

Reaction notes

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