p-Toluenesulfonic acid → HCID 19991747, compound

HRID 345999Notes

Reaction equation

HRID 345999 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([N:19]3[C:24]([CH3:26])([CH3:25])[CH2:23][C:22](=O)[CH2:21][C:20]3([CH3:29])[CH3:28])[N:8]=2)[CH2:3][CH2:2]1.C(OCC)(=O)C.[CH2:36]([NH2:40])[CH2:37][CH2:38][CH3:39].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pt]>[O:16]1[CH2:15][CH2:14][N:13]([C:11]2[N:12]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:8]=[C:9]([N:19]3[C:20]([CH3:29])([CH3:28])[CH2:21][CH:22]([NH:40][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:23][C:24]3([CH3:26])[CH3:25])[N:10]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8007ButylamineHCID 8857Ethyl AcetateHCID 19991750HCID 19991750, compound2×

Product 1

HCID 19991747HCID 19991747, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

12 g of 2,4-bis-morpholino-6-(4-oxo-2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine (product from Example 21) are hydrogenated in 120 ml of methanol and 60 ml of ethyl acetate at 40° and a pressure of 80 bar with 5% platinum on charcoal as the catalyst in the presence of 6 g of butylamine and 0.25 g of p-toluenesulfonic acid until the reaction has ended. The reaction mixture is filtered and evaporated. After dissolving the residue in methylene chloride and washing with water, the organic phase is dried over Na2SO4 and evaporated. The residue is dissolved in toluene/acetone and purified chromatographically on an SiO2 column. The oily product crystallizes after a few days and melts at 82°-87°.

Workup

  1. customat 40°
  2. filtrationThe reaction mixture is filtered
  3. customevaporated
  4. dissolutionAfter dissolving the residue in methylene chloride
  5. washwashing with water
  6. dry with materialthe organic phase is dried over Na2SO4
  7. customevaporated
  8. dissolutionThe residue is dissolved in toluene/acetone
  9. custompurified chromatographically on an SiO2 column
  10. customThe oily product crystallizes after a few days

Sources & evidence

ORD record
ord-8b635088b8df465894aa682cf41c289f
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

Loading…