Ammonia → HCID 69522837, compound

HRID 1181442Notes

Reaction equation

HRID 1181442 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N>C(O)C.[Pd].O>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[CH:14][C:11]=2[CH2:12][NH2:13])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 695226892-(2-Morpholin-4-ylethoxy)-4-(trifluoromethyl)benzonitrile

Product 1

HCID 69522837HCID 69522837, compoundYield 96.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(2-morpholin-4-ylethoxy)-4-(trifluoromethyl)benzonitrile (Description 124, 0.5 g, 1.67 mmol) in ethanol (30 ml) was added aqueous ammonia (33% aq soln, 5 ml) and a slurry of 10% Pd/C catalyst in water. The reaction was hydrogenated at 43 psi. After 45 min the reaction was complete. The catalyst was filtered off, the reaction condensed and the product azeotroped with toluene to give the desired amine (0.49 g, 96%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe reaction condensed
  3. customthe product azeotroped with toluene

Sources & evidence

ORD record
ord-2e891430cff0476b8620c88184db3454
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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