Methanol → HCID 20368928, compound

HRID 616770Notes

Reaction equation

HRID 616770 reaction equation
[ClH:1].[OH:2][C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:8][CH2:7][N:6]([CH:9]([F:23])[CH2:10][CH:11]([N+:20]([O-])=O)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH2:5][CH2:4]1.CO>[Pd].[H][H]>[ClH:1].[OH:2][C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[CH2:8][CH2:7][N:6]([CH:9]([F:23])[CH2:10][CH:11]([NH2:20])[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 887MethanolHCID 20368941HCID 20368941, compound

Product 1

HCID 20368928HCID 20368928, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of 4.9 g of γ-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino]-4-fluoro-2-nitrobutyrophenone hydrochloride, 1.0 g of 5 % palladium on charcoal (50 % wet reagent) and 80 g of methanol was vigorously stirred in hydrogen atmosphere at room temperature until the theoretical amount of hydrogen was consumed. The catalyst was filtered off and washed with hot methanol, and the filtrate was concentrated under reduced pressure. The residual solid was triturated with isopropanol, collected by filtration and washed with diisopropyl ether to afford 3.9 g of γ-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino]-2-amino-4-fluorobutyrophenone monohydrochloride. M.P. 202°-204° C. The free base of this product was obtained by the conventional procedure. M.P. 106°-107° C (recrystallized from toluene).

Workup

  1. customwas consumed
  2. filtrationThe catalyst was filtered off
  3. washwashed with hot methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residual solid was triturated with isopropanol
  6. filtrationcollected by filtration
  7. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-abfc132730084159b62b5ded243264c7
Source dataset
uspto-grants-1978_02
Patent number
US04075346

Reaction notes

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