HCID 15858426, compound → HCID 15858428, compound

HRID 1419069Notes

Reaction equation

HRID 1419069 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][NH:12][C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][CH:16]=[CH:17][CH:18]=3)[C:4]=2[O:3]1>C(O)(=O)C.[Pt]=O>[CH3:1][C:2]1([CH3:25])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][NH:12][CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH:14]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 15858426HCID 15858426, compound

Product 1

HCID 15858428HCID 15858428, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

9.2 g of 3-[(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methyl]amino-2-phenylpyridine was dissolved in 120 ml of acetic acid, and 1 g of platinum oxide was added. A hydrogenation reaction was carried out at 3 atmospheric pressure for 8.5 hours. After completion of the reaction, the catalyst was filtered off and the solvent was concentrated. After adding ice pieces to the residue and alkalizing it with 50% aqueous sodium hydroxide solution, it was extracted three times with dichloromethane. After drying the extract solution, it was distilled off and purified by a silica gel chromatography (dichloromethane/methanol 30:1-10:1-3:1) to obtain 3.7 g of oily 3-[(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methyl]amino-2-phenylpiperidine.

Workup

  1. customA hydrogenation reaction
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe solvent was concentrated
  5. additionAfter adding ice pieces to the residue
  6. extractionwas extracted three times with dichloromethane
  7. customAfter drying the extract solution, it
  8. distillationwas distilled off
  9. custompurified by a silica gel chromatography (dichloromethane/methanol 30:1-10:1-3:1)

Sources & evidence

ORD record
ord-ad6a1e642728406ca0297ab7f47503d0
Source dataset
uspto-grants-1999_03
Patent number
US05886011

Reaction notes

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