Ethanol → HCID 12788430, compound

HRID 2295435Notes

Reaction equation

HRID 2295435 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[C@H:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4]1.C(O)C.[H][H]>[Pd].CCOCC>[ClH:1].[NH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][C@H:6]1[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][C@H:5]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 12788426HCID 12788426, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12788430HCID 12788430, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.6 g of cis-1-methyl-4-(3-nitrophenoxy)-3-phenylpiperidine hydrochloride of Example 18, in 110 ml of 190 proof ethanol is hydrogenated at 45 psi of hydrogen and room temperature over 0.46 g of 10% palladium on carbon catalyst. Hydrogen uptake stops after 2.5 hours. The catalyst is filtered off, and the filtrate is concentrated in vacuo to afford a foam which solidifies upon trituration with ether to afford a crude solid, mp s 232°, 249.5° C. dec, This material is recrystallized from absolute ethanol by boiling the filtered solution down, cooling, filtering and washing with absolute ethanol and then ether to yield cis-4-(3-aminophenoxy)-1-methyl-3-phenylpiperidine hydrochloride, mp 259°-260.5° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto afford a foam which
  4. customto afford a crude solid, mp
  5. customs 232°
  6. custom249.5° C. dec, This material is recrystallized from absolute ethanol
  7. temperaturecooling
  8. filtrationfiltering
  9. washwashing with absolute ethanol

Sources & evidence

ORD record
ord-8f71d8380fbb471ba86a1e3bd3018969
Source dataset
uspto-grants-1984_01
Patent number
US04424357

Reaction notes

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