HCID 24809784, compound → HCID 24809748, compound

HRID 886699Notes

Reaction equation

HRID 886699 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([CH2:14][NH:15]CC1C=CC=CC=1)([OH:13])[CH2:4][NH:5]CC1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:5][CH2:4][C:3]([CH2:14][NH2:15])([OH:13])[C:2]([F:24])([F:23])[F:1]

Participants

4

Reactant 1

HCID 24809784HCID 24809784, compound

Product 1

HCID 24809748HCID 24809748, compoundYield 126.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1,1-trifluoro-3-[(phenylmethyl)amino]-2-{[(phenylmethyl)amino]methyl}-2-propanol (8.15 g, 24.1 mmol) in ethanol (200 ml) was stirred under a hydrogen atmosphere over Pearlman's catalyst (500 mg) for 24 hours. The catalyst was filtered off and the filtrate concentrated under reduced pressure. The residue was redissolved in methanol and concentrated under reduced pressure to give an oil (4.825 g). This oil was redissolved in ethanol (200 ml) and stirred under a hydrogen atmosphere over Pearlman's catalyst (500 mg) for 24 hours. The catalyst was filtered off and the filtrate concentrated under reduced pressure to give the title compound (3.07 g) as an oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionThe residue was redissolved in methanol
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee27eea38ff441758a42de3338a928bf
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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