HCID 23370065, compound → HCID 23370086, compound

HRID 1901072Notes

Reaction equation

HRID 1901072 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:13]([OH:20])=[C:12]([C:21]([CH3:23])([CH3:22])[CH3:24])[CH:11]=1

Participants

4

Reactant 1

HCID 23370065HCID 23370065, compound

Product 1

HCID 23370086HCID 23370086, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 4-[3-(2-nitrophenoxy)propyl]-2,6-di-t-butylphenol (1.03 g) in ethanol (30 ml) was added a catalytic amount of 10% palladium/carbon to carry out catalytic reduction under 3-4 arms at 40° C. for 10 hrs. After filtering off the catalyst, the solvent was distilled off to give 4-[3-(2-aminophenoxy)propyl]-2,6-di-t-butylphenol. This compound was dissolved in dichloromethane (20 ml), to which diisopropylamine (0.75 ml) was added. Phenyl chloroformate (0.84 g) was added dropwise under ice-cooling. After stirring the mixture at room temperature overnight, the reaction solution was washed with water and then saturated saline and dried over anhydrous MgSO4. After distilling off the solvent, the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=15:1) to give 1-(1-benzyl-4-piperidyl)-3-[2-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propoxy]phenyl]urea (1.23 g, 97%).

Workup

  1. customat 40° C.
  2. customfor 10 hrs
  3. filtrationAfter filtering off the catalyst
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2159bd6e50144a619b8d0076cebf4f79
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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