HCID 20321974, compound → HCID 20321972, compound

HRID 839780Notes

Reaction equation

HRID 839780 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][C:6]=1[C:7]([N:9]([CH3:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:8]>[Pt].C(O)(=O)C>[F:29][C:2]([F:1])([F:28])[CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][C:6]=1[C:7]([N:9]([CH3:17])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]1)=[O:8]

Participants

4

Reactant 1

HCID 20321974HCID 20321974, compound

Product 1

HCID 20321972HCID 20321972, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

2,5-Bis(2,2,2-trifluoroethoxy)-N-methyl-N-(2-pyridylmethyl)benzamide (0.015 mole, 6.33 g.) in 200 ml. of glacial acetic acid is mixed with 0.2 g. of platinum oxideacetic acid paste and the mixture is shaken on a Parr hydrogenation apparatus at a temperature of about 23° C. for about 3.5 hours. The resulting material is filtered and the filtrate is evaporated, toluene being added to form an azeotrope and facilitate evaporation. The residue of the evaporation is mixed with 5 percent sodium hydroxide solution and diethyl ether, and the organic layer is separated, washed with saturated sodium chloride solution, dried and evaporated to provide a white solid, 2,5-bis(2,2,2-trifluoroethoxy)-N-methyl-N-(2-piperidylmethyl)benzamide, m.p. 104°-107° C.

Workup

  1. filtrationThe resulting material is filtered
  2. customthe filtrate is evaporated
  3. additiontoluene being added
  4. customto form an azeotrope
  5. customevaporation
  6. customThe residue of the evaporation
  7. additionis mixed with 5 percent sodium hydroxide solution and diethyl ether
  8. customthe organic layer is separated
  9. washwashed with saturated sodium chloride solution
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-50ee538524ca45e2867261c604b0a989
Source dataset
uspto-grants-1978_06
Patent number
US04097481

Reaction notes

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