Thiophene → HCID 67823130, compound

HRID 359416Notes

Reaction equation

HRID 359416 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1[CH:5]=[C:6]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH:7]=[CH:8][CH:9]=1.[C:24]([O-])(=[O:26])C.[K+].S1C=CC=[CH:30]1.[H][H]>CO.[Pd]>[OH2:26].[ClH:1].[ClH:1].[CH3:24][N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH3:3])[CH:5]=1)[CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16]1.[CH3:30][N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH3:3])[CH:5]=1)[CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16]1.[ClH:1].[ClH:1]

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 19095528HCID 19095528, compoundHCID 178418361HCID 178418361, compoundHCID 178486302HCID 178486302, compound

Product 1

HCID 67823130HCID 67823130, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 21 parts of N-(3-methylphenyl)-1-(phenylmethyl)-4-piperidinamine dihydrochloride, 9 parts of poly(oxymethylene), 15 parts of potassium acetate, 2 parts of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over Hyflo and the filtrate was evaporated. From the residue, the free base was liberated with ammonium hydroxide and extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried, yielding 2.4 parts (75%) of N-methyl-N-(3-methylphenyl)-1-(phenylmethyl)-4-piperidinamine dihydrochloride hemihydrate; mp. 201.3° C. (intermediate 96).

Workup

  1. filtrationthe catalyst was filtered off over Hyflo
  2. customthe filtrate was evaporated
  3. extractionextracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. filtrationThe salt was filtered off
  12. customdried

Sources & evidence

ORD record
ord-907b37007b39428b97ecccc59b6c3280
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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