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

HRID 929893Notes

Reaction equation

HRID 929893 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 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. customdried

Sources & evidence

ORD record
ord-1638e71480444c41aed3ffd0175b3ed1
Source dataset
uspto-grants-2016_03
Patent number
US09296723B2

Reaction notes

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