HCID 19696461, compound → HCID 19696462, compound

HRID 863464Notes

Reaction equation

HRID 863464 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][N:6]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][N:6]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9]

Participants

5

Reactant 2

HCID 19696461HCID 19696461, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19696462HCID 19696462, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of step (b) (3.89 g, 10.05 mmol) in ethyl acetate (100 ml) was added 5% Pd/C. The mixture was hydrogenated at 50 psig for 1.4 hours, until the theoretical amount of hydrogen was taken up. The catalyst was filtered and the filtrate concentrated to an oil. This was purified by chromatography (silica gel, methylene chloride: n-hexane (1:1)) to yield 2.33 g of pure N-(3-chlorobenzyl)-N-(2-(4-aminophenyl)ethyl)trifluoroacetamide as a thick oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated to an oil
  3. customThis was purified by chromatography (silica gel, methylene chloride: n-hexane (1:1))

Sources & evidence

ORD record
ord-4d449676d0094e3785748dd0bdb3b7f0
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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