Hydrochloric Acid → HCID 12788411, compound

HRID 851013Notes

Reaction equation

HRID 851013 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C@H:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C@H:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1.[H][H].[ClH:26]>C(O)C.[Pd].CCOCC>[ClH:26].[ClH:26].[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C@H:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C@H:4]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12788399HCID 12788399, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12788411HCID 12788411, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3.7 g of the free base of cis-1-methyl-4-(4-nitrophenoxy)-3-phenylpiperidine, of Example 7, in 100 ml of absolute ethanol is hydrogenated over 0.37 g of 10% Pd on carbon catalyst at 45 psi of hydrogen and room temperature. Uptake stops after 48 hours. The catalyst is filtered off and the filtrate is concentrated in vacuo to a gum. This material is chromatographed on silica gel using acetone and then 25% methanol/acetone as solvent. A purified free base is obtained and a portion of this material is dissolved in ether and is then added dropwise to a solution of dry HCl in ether. The resulting precipitate is filtered, washed with ether, and is then immediately suspended in boiling ether. Absolute ethanol is added until the mixture grows clear. Scratching of the cold solution causes crystallization to occur. The recrystallized solid is filtered, washed with cold acetone, then ether, and dried to afford a solid (m.p. 226°-227° C. dec.) of cis-4-(4-aminophenoxy)-1-methyl-3-phenylpiperidine dihydrochloride.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo to a gum
  3. customThis material is chromatographed on silica gel
  4. customA purified free base is obtained
  5. filtrationThe resulting precipitate is filtered
  6. washwashed with ether
  7. additionAbsolute ethanol is added until the mixture
  8. customcrystallization
  9. filtrationThe recrystallized solid is filtered
  10. washwashed with cold acetone
  11. dry with materialether, and dried

Sources & evidence

ORD record
ord-6bf4aedf4dfa4b6eb8e07ddabb4f7196
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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