2,2,2-trifluoro-N-[4-(pyridin-4-ylmethyl)phenyl]acetamide → 2,2,2-trifluoro-N-(4-(piperidin-4-ylmethyl)-phenyl]acetamide

HRID 873602Notes

Reaction equation

HRID 873602 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:4]>[Pt](=O)=O.C(O)(=O)C>[F:20][C:2]([F:1])([F:19])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 1

HCID 7543052,2,2-trifluoro-N-[4-(pyridin-4-ylmethyl)phenyl]acetamide

Product 1

HCID 218767392,2,2-trifluoro-N-(4-(piperidin-4-ylmethyl)-phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

2,2,2-Trifluoro-N-(4-(pyridin-4-ylmethyl)phenyl)acetamide (28.5 g, 102 mmol) and acetic acid (205 ml) were added to platinum(IV) oxide (3.42 g, 15.06 mmol) in a 500 mL stainless steel pressure bottle and the mixture was stirred for 16 hours at 40 psi. The mixture was filtered through a nylon membrane and concentrated in vacuo; and the resulting residue was taken up in methanol (100 mL) and poured into diethyl ether (600 mL). The precipitate was filtered, washed with ether and dried with sodium sulfate to afford the title compound.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated in vacuo
  3. additionpoured into diethyl ether (600 mL)
  4. filtrationThe precipitate was filtered
  5. washwashed with ether
  6. dry with materialdried with sodium sulfate

Sources & evidence

ORD record
ord-1ead0ab4f867497e81888624cd9ea731
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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