Piperidin-4-ol → (+/-)-2-[3-chloro-4-[(4-chlorophenyl)(4-hydroxy-1-piperidinyl) methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione

HRID 984047Notes

Reaction equation

HRID 984047 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[OH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[N:29]1[CH2:30][CH2:31][CH:26]([OH:25])[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 516892Sodium BicarbonateHCID 225573573-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 22557329(+/-)-2-[3-chloro-4-[(4-chlorophenyl)(4-hydroxy-1-piperidinyl) methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dioneYield 1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.015 mol), 4-hydroxypiperidine (0.02 mol) and sodiumbicarbonate (0.02 mol) in DMF (100 ml) was stirred for 16 hours at 80° C. The mixture was cooled. The solvent was evaporated. The residue was purified by columnchromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The desired fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off and dried, yielding 0.070 g (±)-2-[3-chloro-4-[(4-chlorophenyl)(4-hydroxy-1-piperidinyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (compound 119).

Workup

  1. temperatureThe mixture was cooled
  2. customThe solvent was evaporated
  3. customThe residue was purified by columnchromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  4. customThe desired fractions were collected
  5. customthe solvent was evaporated
  6. stirringThe residue was stirred in DIPE
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-46e46b887aa9446b83ed91247aaf54c1
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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